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

HRID 1602983Notes

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]

Participants

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

temperaturecooled to 0° C.
customThe mixture was partitioned between ethyl acetate and water
washthe organic phase was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
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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