Citric Acid → (2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane

HRID 2301743Notes

Reaction equation

HRID 2301743 reaction equation
CC(O)C.[C:5]([O:9][C:10]([NH:12][C@@H:13]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@H:14]([OH:17])[CH2:15]Cl)=[O:11])([CH3:8])([CH3:7])[CH3:6].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[C:5]([O:9][C:10]([NH:12][C@@H:13]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@@H:14]1[O:17][CH2:15]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 71466451,1-Dimethylethyl N-((1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl)carbamate

Product 1

HCID 9903372(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutaneYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

2-Propanol (2.4 ml) was added to (2S,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane (300 mg). After the mixture was cooled to 4° C., an aqueous solution (0.375 ml) of 4 mols/liter of sodium hydroxide and water (0.225 ml) were added thereto, and the mixture was stirred at 4° C. for 7 hours. After a 13.7% citric acid aqueous solution (695 mg) was added thereto, the mixture was extracted with tert-butylmethyl ether. The resulting organic layer was washed with water. It was identified by HPLC analysis that desired (2S,3S)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane (230 mg) was obtained in a yield of 87%.

Workup

  1. extractionthe mixture was extracted with tert-butylmethyl ether
  2. washThe resulting organic layer was washed with water
  3. customwas obtained in a yield of 87%

Sources & evidence

ORD record
ord-50dc4c36961c4981a0883e71c73f4178
Source dataset
uspto-grants-2002_12
Patent number
US06500985B2

Reaction notes

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