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

HRID 388446ノート

反応式

HRID 388446 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-f98f80d3a0c34d2784e468ed5d3a17ab
出典データセット
uspto-grants-2013_02
特許番号
US08377949B2

反応ノート

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