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

HRID 1169245Notes

Reaction equation

HRID 1169245 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. 1H NMR (300 mHz, DMSO-d6) δ7.4-7.2 (m, 5H), 3.87 (q, J=6.6 Hz, 1H), 3.27 (dd, J=13.6, 7.0 Hz, 1H), 3.0-2.8 (m, 3H), 2.5 (m, 2H), 1.26 (d, J=6.6, 3H), ESI MS: (M+H)+252.0.

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-33db249a44dd4f5a9aafd48ae7c07cb6
Source dataset
uspto-grants-2003_09
Patent number
US06627629B2

Reaction notes

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