Dichloromethane → 2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methyl-butanoic acid hydrochloride

HRID 1720575Notes

Reaction equation

HRID 1720575 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[C@H:13]([CH:21]([CH3:23])[CH3:22])[C:14]([O:16]C(C)(C)C)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)[Cl:32]>>[ClH:32].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[C@H:13]([CH:21]([CH3:23])[CH3:22])[C:14]([OH:16])=[O:15])(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 11797104t-Butyl 2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanoate

Product 1

HCID 700617032(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methyl-butanoic acid hydrochloride

Conditions

Temperature
10 °C

Procedure

t-Butyl 2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanoate (5.3 g, 12.2 mmol) is dissolved in methylene chloride (150 mL) and cooled to-10° C. Hydrochloric acid gas is bubbled into the solution for 10 minutes. The reaction mixture is then sealed, warmed to room temperature and stirred for 4 hours. The solvent is then evaporated to provide 2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanoic acid hydrochloride.

Workup

  1. customHydrochloric acid gas is bubbled into the solution for 10 minutes
  2. customThe reaction mixture is then sealed
  3. temperaturewarmed to room temperature
  4. customThe solvent is then evaporated

Sources & evidence

ORD record
ord-e6d8c332a2dd41e6b14cbe25086b05b5
Source dataset
uspto-grants-1996_04
Patent number
US05506242

Reaction notes

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