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Sodium Bisulfate → S-methyl--N--[4-(phenoxy)benzenesulfonyl]-D-penicillamine

HRID 1602983
Notes
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Reaction equation

HRID 1602983 reaction equation
C[O:2][C:3](=[O:27])[C@@H:4]([C:22]([S:25][CH3:26])([CH3:24])[CH3:23])[NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7].C[S-].[Na+].S(=O)(=O)(O)[O-].[Na+]>CS(C)=O>[CH3:26][S:25][C:22]([CH3:24])([CH3:23])[C@H:4]([C:3]([OH:27])=[O:2])[NH:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:13][CH:14]=1)(=[O:7])=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516919Sodium BisulfateHCID 4378561Sodium methanethiolateHCID 57188101S-methyl--N--[4-(phenoxy)benzenesulfonyl]-D-penicillamine methyl ester

Product 1

HCID 56999283S-methyl--N--[4-(phenoxy)benzenesulfonyl]-D-penicillamineYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl Sulfoxide
Solvent

Conditions

Temperature
45 °C

Procedure

To a solution of S-methyl--N--[4-(phenoxy)benzenesulfonyl]-D-penicillamine methyl ester (0.250 g., 0.610 mmol) in DMSO (3 mL) at room temperature was added sodium thiomethoxide (171 mg., 2.44 mmol) in one portion. The solution was heated at 45° C. for18 hours, and then cooled to 0° C. and acidified to pH=5 using 1N aqueous sodium bisulfate. The mixture was partitioned between ethyl acetate and water, and the organic phase was washed with brine, dried over MgSO4, and concentrated. The residue was purified on silica eluting with 8 to 12% methanol in dichloromethane to give S-methyl--N--[4-(phenoxy)benzenesulfonyl]-D-penicillamine as a white solid in 95% yield: mp 156-158° C.; 1H--NMR (DMSO-d6) δ 1.28 (s, 3H), 1.31 (s, 3H), 1.97 (s,3H), 7.08-7.82 (m, 10H).

Workup

  1. temperaturecooled to 0° C.
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washthe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on silica eluting with 8 to 12% methanol in dichloromethane

Sources & evidence

ORD record
ord-cef2495fb0004b9ebf6973f449b780ef
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05985900

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes