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

HRID 388446Notes

Reaction equation

HRID 388446 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-f98f80d3a0c34d2784e468ed5d3a17ab
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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