HCID 66704226, compound → HCID 66704245, compound

HRID 1661869Notes

Reaction equation

HRID 1661869 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([C:32](=[O:34])[NH2:33])([CH2:18][C:19]([O:21][CH:22]1[CH:27]([CH:28]([CH3:30])[CH3:29])[CH2:26][CH2:25][CH:24]([CH3:31])[CH2:23]1)=[O:20])[C:13]([O:15][CH2:16][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:32](=[O:34])[NH2:33])([CH2:18][C:19]([O:21][CH:22]1[CH:27]([CH:28]([CH3:30])[CH3:29])[CH2:26][CH2:25][CH:24]([CH3:31])[CH2:23]1)=[O:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 66704226HCID 66704226, compound

Product 1

HCID 66704245HCID 66704245, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

Acetone (750 g) was added to ethyl 2-benzyloxycarbonylamino-2-carbamoyl-3-[(−)-menthyloxycarbonyl]propionate (150 g, 0.315 mol) and the mixture was heated to 40° C., the solid was dissolved and then the solution was gradually cooled. It was placed to be matured at 10° C. overnight and then stirred at 5° C. for about an hour. The crystals were filtered, washed with sprayed cold acetone (50 ml×2) and dried in airflow at 60° C. to give ethyl (2R)-2-benzyloxycarbonylamino-2-carbamoyl-3-[(−)-menthyloxycarbonyl]propionate (57.9 g). mp. 124° C., yield 38.6%: optical purity (HPLC) 98.8% d.e.

Workup

  1. dissolutionthe solid was dissolved
  2. temperaturethe solution was gradually cooled
  3. filtrationThe crystals were filtered
  4. washwashed
  5. customdried in airflow at 60° C.

Sources & evidence

ORD record
ord-0e00f459df2f4be3b3c1724c8da0d5c4
Source dataset
uspto-grants-2011_10
Patent number
US08030486B2

Reaction notes

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