Hydrochloric Acid → (2S,3S)-3-[[1-(S)-[alpha-(R)-hydroxybenzyl]-3-methylbutyl]-carbamoyl]oxirane-2-carboxylic acid

HRID 1935414Notes

Reaction equation

HRID 1935414 reaction equation
[OH:1][C@@H:2]([C@@H:9]([NH:14][C:15]([C@H:17]1[O:19][C@@H:18]1[C:20]([O:22]CC)=[O:21])=[O:16])[CH2:10][CH:11]([CH3:13])[CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[K+].C(O)C.O.Cl>C(O)C>[OH:1][C@@H:2]([C@@H:9]([NH:14][C:15]([C@H:17]1[O:19][C@@H:18]1[C:20]([OH:22])=[O:21])=[O:16])[CH2:10][CH:11]([CH3:12])[CH3:13])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 12051467Ethyl (2S,3S)-3-[[1-(S)-[alpha-(R)-hydroxybenzyl]-3-methyl-butyl]carbamoyl]oxirane-2-carboxylateHCID 21946426Potassium hydroxide ethanol

Product 1

HCID 12051469(2S,3S)-3-[[1-(S)-[alpha-(R)-hydroxybenzyl]-3-methylbutyl]-carbamoyl]oxirane-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (2S,3S)-3-[[1-(S)-[α-(R)-hydroxybenzyl]-3-methylbutyl]carbamoyl]oxirane-2-carboxylate (558 mg, 1.66 mmol.) in ethanol (4 mL) was dropwise added 0.5N potassium hydroxide/ethanol solution (4.0 mL, 2.0 mmol.) under chilling with ice. The mixture was stirred for 4 hours at room temperature, and made acidic to reach pH 1-2 by addition of water (40 mL) and 2N hydrochloric acid (approx. 2 mL). The acidic mixture was extracted with three portions of ethyl acetate. The three extracts were combined and washed successively with water and an aqueous saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give the titled compound as a white amorphous product (490 mg, yield 96%).

Workup

  1. temperatureunder chilling with ice
  2. extractionThe acidic mixture was extracted with three portions of ethyl acetate
  3. washwashed successively with water
  4. dry with materialan aqueous saturated sodium chloride solution, and then dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5b4928cc5d4540868ac05136e1778fa5
Source dataset
uspto-grants-2002_05
Patent number
US06387908B1

Reaction notes

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