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n, n-diethyl-formic acid 4-halomethyl-3,5-dimethyl-phenol ester compound and preparation method thereof

A technology of dimethyl phenol and diethyl chloroformamide, which is applied in the field of compounds, can solve the problems of insufficient alkylation activity, low efficiency, and increased costs, and achieve the effect of simple and easy scale-up preparation

Inactive Publication Date: 2017-03-01
SULI CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] (2) The alkylation activity of compound 1 is not enough, and it cannot be directly used in the alkylation reaction. It needs to be converted into the corresponding iodide 2 and then alkylated. The synthesis efficiency is not high, and the cost is increased.

Method used

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  • n, n-diethyl-formic acid 4-halomethyl-3,5-dimethyl-phenol ester compound and preparation method thereof
  • n, n-diethyl-formic acid 4-halomethyl-3,5-dimethyl-phenol ester compound and preparation method thereof
  • n, n-diethyl-formic acid 4-halomethyl-3,5-dimethyl-phenol ester compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0040] Preparation Example 1: Preparation of Compound 5

[0041] Dissolve 3,5-dimethylphenol 3 (21.8 g, 0.178 mol, 1.0 equiv) in acetonitrile (160 mL), add K 2 CO 3 (34.2g, 0.248mol, 1.4eq) and N,N-diethylchloroformamide (34.6g, 0.255mol, 1.43eq). The reaction mixture was heated to reflux for 7.5h. HPLC control showed less than 2% starting material. The reaction solution was cooled to room temperature and then filtered. The filter cake was washed with acetonitrile (50 mL). The filtrate was concentrated to 50 mL, and then diluted with methyl tert-butyl ether (200 mL). The solution was washed sequentially with 1M hydrochloric acid (100 mL), 3% aqueous NaHCO3 (100 mL), 10% NaCl (100 mL) and water (100 mL). The organic phase was concentrated to obtain crude product 6 (39.7 g, 90.4% purity) which was directly used in the next step. H-NMR (CD 3 Cl, 400MHz): 6.81(s, 1H), 6.71(s, 2H), 3.48(m, 4H), 2.25(s, 6H), 1.19(m, 6H).

[0042] To the reaction flask was added 6 (68 g, 0.28...

preparation Embodiment 2

[0043] Preparation Example 2: Preparation of Compound 7

[0044] To a round bottom flask was added compound 5 (2976 mg, 10.9 mmol), NaI (3268 mg, 2 eq) and acetone (22 mL). After the reaction was carried out at 40°C for 16 hours, it was cooled to 20°C, and water was added to the reaction solution to cause precipitation. The system was cooled to 5°C. The precipitate was filtered and washed with a mixed solvent of acetone and water (V / V=1 / 2, 15 mL). The filter cake was dried under reduced pressure to obtain product 7 (3411 mg, 82% yield) as a pale yellow solid.

preparation Embodiment 3

[0045] Preparation Example 3: Preparation of Compound 2

[0046]3,5-Dimethylphenol 3 (123.4g, 1.0mol), the dichloromethane (500mL) solution of triethylamine (104g, 1.03mol) and 4-dimethylaminopyridine (1.24g, 0.01mol) is cooled to At 0°C, ethyl chloroformate (116.3 g, 1.05 mol) was added dropwise, and the dropwise addition temperature was controlled at 10-30°C. The reaction was completed at 20-30°C for 4 hours. Water (200mL) was added to the reaction solution, and the organic phase was washed twice with 1N hydrochloric acid (200mL) after phase separation, and 5% NaHCO 3 Wash twice with aqueous solution (200 mL) and finally with water (200 mL). The organic phase was concentrated to give oil 4 (98% yield, 98.6% purity) which was directly used in the next step.

[0047] Add compound 4 (29.5g, 0.149mol), ethylene glycol dimethyl ether (60g), 37% aqueous formaldehyde (33.3g, 0.411mol, 2.8equiv.), zinc chloride in a round bottom flask equipped with mechanical stirring (20.3 g, 0...

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Abstract

The invention relates to an N,N-diethyl-formic acid 4-halogenate methyl-3,5-dimethyl-phenol ester compound and a preparing method thereof. The compound is used for synthesis of dimethyl tyrosine. The compound is more effective than compounds involved in the prior art, it is presented that the preparation of the compound facilitates production amplifying more easily and the reactivity of the dimethyl tyrosine prepared through the compound is higher, additional reaction activation steps or activation reagents are not needed, and therefore the compound is more economical and effective.

Description

technical field [0001] The present invention relates to the field of compounds, in particular to a novel compound N,N-diethyl-formic acid 4-halomethyl-3,5-dimethyl-phenol ester and a method for preparing the compound [0002] technical background [0003] Dimethyltyrosine is an important class of unnatural amino acids. The synthesis of this compound is carried out by an alkylation reaction of the compound shown below. (See Tetrahedron Asymmetry 2000, 11, 2917-2925; Tetrahedron Asymmetry 2009, 20, 1398-1401; US4603121): [0004] (where X is a leaving group and R is a protecting group). [0005] This type of compound reported in the literature has the following two compounds: [0006] [0007] These two compounds have the following defects as synthetic intermediates: [0008] (1) These two compounds are both oily, and it is difficult to scale up production and purification. In the process of preparing compound 1, the protecting group will be partially removed. After t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C271/44C07C269/00C07C271/22C07C269/04
Inventor 费仲波吴志西山章武田俊弘满田胜
Owner SULI CO LTD
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