Ethyl 2-(tert-butoxycarbonylamino)-2-carbamoyl-3-[(-)-menthyloxycarbonyl]propionate → ethyl (2R)-2-(tert-butoxycarbonylamino)-2-carbamoyl-3-[(-)-menthyloxycarbonyl]propionate

HRID 426026Notes

Reaction equation

HRID 426026 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([C:29](=[O:31])[NH2:30])([CH2:15][C:16]([O:18][CH:19]1[CH:24]([CH:25]([CH3:27])[CH3:26])[CH2:23][CH2:22][CH:21]([CH3:28])[CH2:20]1)=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(C)=O>[C:1]([O:5][C:6]([NH:8][C@@:9]([C:29](=[O:31])[NH2:30])([CH2:15][C:16]([O:18][CH:19]1[CH:24]([CH:25]([CH3:26])[CH3:27])[CH2:23][CH2:22][CH:21]([CH3:28])[CH2:20]1)=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 66704183Ethyl 2-(tert-butoxycarbonylamino)-2-carbamoyl-3-[(-)-menthyloxycarbonyl]propionate

Product 1

HCID 66704283ethyl (2R)-2-(tert-butoxycarbonylamino)-2-carbamoyl-3-[(-)-menthyloxycarbonyl]propionateYield 11.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 2-(tert-butoxycarbonylamino)-2-carbamoyl-3-[(−)-menthyloxycarbonyl]propionate (737 mg, 1.67 mmol) was dissolved in acetone (3.69 g) and the solution was placed at 5-10° C. The precipitated crystals were filtered to give ethyl (2R)-2-(tert-butoxycarbonylamino)-2-carbamoyl-3-[(−)-menthyloxycarbonyl]propionate (88 mg) as a white crystal. mp. 176° C., optical purity: 82.6% d.e.

Workup

  1. customwas placed at 5-10° C
  2. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-e0117ddeae3d44159027010fea7969da
Source dataset
uspto-grants-2012_01
Patent number
US08106230B2

Reaction notes

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