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

HRID 2120141Notes

Reaction equation

HRID 2120141 reaction equation
[OH:1][C@@H:2]([C@@H:9]([NH:14][C:15]([O:17]C(C1CO1)=O)=O)[CH2:10][CH:11]([CH3:13])[CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-:23].[K+].[CH2:25]([OH:27])[CH3:26].O.Cl.[CH2:30]([OH:32])C>>[OH:1][C@@H:2]([C@@H:9]([NH:14][C:15]([C@H:26]1[O:27][C@@H:25]1[C:30]([OH:32])=[O:23])=[O:17])[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 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 21946426Potassium hydroxide ethanolHCID 86585457[1-(S)-[alpha-(R)-hydroxybenzyl]-3-methylbutyl carbamoyl]oxirane-2-carboxylate

Product 1

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

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 m) 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 The mixture
  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-148a037393904f8baac01f5e6bb49111
Source dataset
uspto-grants-2004_02
Patent number
US06689785B2

Reaction notes

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