Acetone → t-Butyl 2-benzyloxycarbonylamino-2-carbamoyl-3-[(-)-menthyloxycarbonyl]propionate

HRID 1661873Notes

Reaction equation

HRID 1661873 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([C:34]#[N:35])([CH2:20][C:21]([O:23][CH:24]1[CH:29]([CH:30]([CH3:32])[CH3:31])[CH2:28][CH2:27][CH:26]([CH3:33])[CH2:25]1)=[O:22])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:38].C(=O)([O-])[O-].[K+].[K+].OO>O>[CH2:1]([O:8][C:9]([NH:11][C:12]([C:34](=[O:38])[NH2:35])([CH2:20][C:21]([O:23][CH:24]1[CH:29]([CH:30]([CH3:31])[CH3:32])[CH2:28][CH2:27][CH:26]([CH3:33])[CH2:25]1)=[O:22])[C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 66704238t-Butyl 2-benzyloxycarbonylamino-2-cyano-3-[(-)-menthyloxycarbonyl]propionate

Product 1

HCID 66704225t-Butyl 2-benzyloxycarbonylamino-2-carbamoyl-3-[(-)-menthyloxycarbonyl]propionateYield 45.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

t-Butyl 2-benzyloxycarbonylamino-2-cyano-3-[(−)-menthyloxycarbonyl]propionate (2.00 g, 4.11 mmol) and acetone (10 ml) were mixed and an aqueous solution of potassium carbonate (566 mg, 5.34 mmol) in water (5.0 ml) was added thereto. Further, 30% aqueous hydrogen peroxide solution (1.6 ml) was added dropwise and the mixture was stirred for about 6 hours. When completion of the reaction was confirmed, water was added and the precipitated crystals were filtered, washed with sprayed water and hexane to give t-butyl 2-benzyloxycarbonylamino-2-carbamoyl-3-[(−)-menthyloxycarbonyl]propionate (950 mg, yield 45.8%) as a pale yellow crystal. Optical purity of (2R)-derivative was 7.4% d.e.

Workup

  1. filtrationthe precipitated crystals were filtered
  2. washwashed with sprayed water and hexane

Sources & evidence

ORD record
ord-29aca1dc805d4b19829967e00539b76e
Source dataset
uspto-grants-2011_10
Patent number
US08030486B2

Reaction notes

Loading…