Hydrochloric Acid → (3R,4S)-4-[(R)-1-phenyl-ethylamino]-tetrahydrothiophene-3-carboxylic acid

HRID 497496Notes

Reaction equation

HRID 497496 reaction equation
C[O:2][C:3]([C@H:5]1[C@H:9]([NH:10][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[CH2:8][S:7][CH2:6]1)=[O:4].[OH-].[Na+].Cl>O1CCCC1>[C:13]1([C@H:11]([NH:10][C@@H:9]2[CH2:8][S:7][CH2:6][C@H:5]2[C:3]([OH:4])=[O:2])[CH3:12])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69750268(3R,4S)-4-[(R)-1-phenyl-ethylamino]-tetrahydrothiophene-3-carboxylic acid methyl ester

Product 1

HCID 69750189(3R,4S)-4-[(R)-1-phenyl-ethylamino]-tetrahydrothiophene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Preparation of (3R,4S)-4-[(R)-1-phenyl-ethylamino]-tetrahydrothiophene-3-carboxylic acid methyl ester (673 mg, 2.54 mmol) in tetrahydrofuran (5 mL) was treated with 1.0 M sodium hydroxide solution (5.0 mL, 5.0 mmol) and the heterogeneous mixture was stirred at room temperature. After 75 min, the now homogeneous solution was treated with 1.0 M hydrochloric acid (5.0 mL, 5.0 mmol) and concentrated in vacuo. The residue was dissolved in water and lyophilized to provide the product, along with sodium chloride, as a fluffy white solid (928 mg, quantitative), used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. customto provide the product
  4. customalong with sodium chloride, as a fluffy white solid (928 mg, quantitative), used without further purification

Sources & evidence

ORD record
ord-7ac431aefd584466a25c4718f7cb0551
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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