Acetyl chloride → methyl (2R)-2-amino-2-cyclohexylacetate hydrochloride

HRID 388487Notes

Reaction equation

HRID 388487 reaction equation
[C:1]([Cl:4])(=O)C.Cl.[NH2:6][C@H:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:8]([OH:10])=[O:9]>CO>[ClH:4].[CH3:1][O:9][C:8](=[O:10])[C@H:7]([NH2:6])[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 54579878(2R)-2-amino-2-cyclohexylacetic acid hydrochloride

Product 1

HCID 56777252methyl (2R)-2-amino-2-cyclohexylacetate hydrochlorideYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of acetyl chloride (0.5 mL, 7.04 mmol) in MeOH (10 mL) at 0° C. is added (R)-amino-cyclohexyl-acetic acid hydrochloride (1.0 g, 5.16 mmol). The mixture is stirred at 60° C. for 16 hours. The reaction mixture is allowed to cool to room temperature and concentrated. The resulting residue is triturated with Et2O to afford the title compound (1.0 g, 93%).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated
  3. customThe resulting residue is triturated with Et2O

Sources & evidence

ORD record
ord-dbabdbd9d0e84ffa8c55a276dc55e2d6
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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