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

HRID 426028Notes

Reaction equation

HRID 426028 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([C:34](=[O:36])[NH2:35])([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>[CH2:1]([O:8][C:9]([NH:11][C@@:12]([C:34](=[O:36])[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]([CH3:18])([CH3:17])[CH3:19])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 66704225t-Butyl 2-benzyloxycarbonylamino-2-carbamoyl-3-[(-)-menthyloxycarbonyl]propionate

Product 1

HCID 66704172t-butyl (2R)-2-benzyloxycarbonylamino-2-carbamoyl-3-[(-)-menthyloxycarbonyl]propionateYield 8.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

t-Butyl 2-benzyloxycarbonylamino-2-carbamoyl-3-[(−)-menthyloxycarbonyl]propionate (500 mg) was dissolved in acetone (2.5 g) under heating and placed in a freezer overnight. The precipitated crystals were filtered and dried to give t-butyl (2R)-2-benzyloxycarbonylamino-2-carbamoyl-3-[(−)-menthyloxycarbonyl]propionate (44 mg, yield 8.8%) as a white crystal. Optical purity of (2R)-derivative: 79.1% d.e.

Workup

  1. temperatureunder heating
  2. filtrationThe precipitated crystals were filtered
  3. customdried

Sources & evidence

ORD record
ord-d2426b1985414888b38c386a1c4973fb
Source dataset
uspto-grants-2012_01
Patent number
US08106230B2

Reaction notes

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