2-Nitrobenzoyl chloride → (R)-cyclohexyl-(2-nitro-benzoylamino)-acetic acid methyl ester

HRID 388446노트

반응식

HRID 388446 반응식
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].Cl.[CH3:14][O:15][C:16](=[O:25])[C@H:17]([NH2:24])[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:14][O:15][C:16](=[O:25])[C@@H:17]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[NH:24][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 118752-Nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 56777252methyl (2R)-2-amino-2-cyclohexylacetate hydrochloride

생성물 1

HCID 68726619(R)-cyclohexyl-(2-nitro-benzoylamino)-acetic acid methyl ester수율 98.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 2-nitrobenzoyl chloride (0.5 mL, 3.69 mmol) and (R)-amino-cyclohexyl-acetic acid methyl ester hydrochloride (1.0 g, 4.82 mmol), (prepared according to example A), in dichloromethane (10 mL) is added diisopropyl ethylamine (DIPEA) (1.5 mL, 8.61 mmol). The mixture is stirred at room temperature for 16 hours. The reaction mixture is concentrated and the resulting residue is purified by flash chromatography with 40% EtOAc in Hexane as the eluent to afford (R)-cyclohexyl-(2-nitro-benzoylamino)-acetic acid methyl ester (1.16 g, 98%).

후처리

  1. concentrationThe reaction mixture is concentrated
  2. customthe resulting residue is purified by flash chromatography with 40% EtOAc in Hexane as the eluent

출처 및 근거

ORD 기록
ord-f98f80d3a0c34d2784e468ed5d3a17ab
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377949B2

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