Chiral alpha-amino acid derivative and preparation method thereof
A technology of chiral amino acids and derivatives, which is applied in the preparation of carbamic acid derivatives, sulfonamides, and organic compounds, and can solve the problems of cumbersome processes, poor applicability, and unsatisfactory catalytic asymmetric synthesis.
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Example Embodiment
[0093] Embodiment 1, the preparation of N, O-acetal
[0094] Method 1: Take CbzNH 2 For the starting material, the branched chain N, O-acetal compound of the target is obtained through the condensation of amine and glyoxylate, and the specific synthesis steps are:
[0095] CbzNH 2 (Benzyl carbamate) and ethyl glyoxylate were mixed in a molar ratio of 1:1.3, acetic acid and acetic anhydride were mixed in a volume ratio of 1:3 as the solvent for the reaction, and stirred at 60 °C for 1 day to remove unreacted Acetic anhydride and acetic acid can obtain the N, O-acetal compound of the corresponding stable branched chain Cbz protecting amine group, and the specific reaction equation is as follows figure 2 shown;
[0096] Method 2: realized by a step-by-step synthesis route, first by CbzNH 2 Condensation with glyoxylate to obtain the hemiacetal of N, O, and then protecting the hydroxyl group with a protecting group, and then obtain the raw material of the acetal of N, O, and th...
Example Embodiment
[0100] Embodiment 2, the preparation of N, O-acetal
[0101] CbzNH 2 (benzyl carbamate) and trichloroacetaldehyde were mixed in a molar ratio of 1:1.3, reacted in ethyl acetate at 60°C for 1 day, and the solvent was removed by rotary evaporation to obtain solid N,O hemiacetal, and then 5 Molar equivalent of acetic anhydride, 1% molar equivalent of pyridine, react at 25°C for 1 day, remove unreacted acetic anhydride, and obtain branched Cbz-protected amine group N,O-acetal compound, specific reaction equation like image 3 shown.
[0102]
[0103] The structure is confirmed as follows: 1 H NMR (400MHz, CDCl 3 )δ7.37(s, 5H), 6.93(d, J=10.0Hz, 1H), 5.69(s, 1H), 5.19(s, 2H), 2.17(s, 3H). 13 C NMR (101MHz, CDCl 3 )δ168.16,135.51,128.80,128.72,128.53,98.21,81.38,68.26,20.69.
Example Embodiment
[0104] Embodiment 3, the preparation of N, O-acetal
[0105] CbzNH 2 (benzyl carbamate), hydrated trifluoroacetaldehyde was mixed at a molar ratio of 1:1.3, reacted in ethyl acetate at 60°C for 1 day, and the solvent was removed by rotary evaporation to obtain a solid N,O hemiacetal, which was then added 5 molar equivalents of acetic anhydride and 1% molar equivalents of pyridine were reacted at 25°C for 1 day, and the unreacted acetic anhydride was removed to obtain a branched Cbz-protected amine group N,O-acetal compound, the specific reaction Equations such as image 3 shown.
[0106]
[0107] The structure is confirmed as follows: 1 H NMR (500MHz, CDCl 3 )δ7.35(q,J=15.0Hz,5H),6.80(s,1H),5.66(d,J=9.0Hz,1H),5.17(d,J=12.0Hz,2H),2.14(s, 3H). 13 C NMR (126MHz, CDCl 3 )δ168.09,154.27,135.26,128.79,128.75,128.53,128.47,122.80,120.57,72.72,72.43,72.14,71.85,68.32,20.52.
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