Sodium Bisulfate → HCID 18395017, compound

HRID 1602987Notes

Reaction equation

HRID 1602987 reaction equation
[CH2:1]([O:4][C:5](=[O:35])[C@@H:6]([C:25]([S:28]CCC(OC)=O)([CH3:27])[CH3:26])[NH:7][S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH:2]=[CH2:3].C[S-].[Na+].S(=O)(=O)(O)[O-].[Na+]>CS(C)=O>[CH2:1]([O:4][C:5](=[O:35])[C@@H:6]([C:25]([SH:28])([CH3:26])[CH3:27])[NH:7][S:8]([C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)=[CH:15][CH:16]=1)(=[O:9])=[O:10])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 516919Sodium BisulfateHCID 4378561Sodium methanethiolateHCID 56995255HCID 56995255, compound

Product 1

HCID 18395017HCID 18395017, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of N-[4-(4-fluorophenoxy)benzenesulfonyl]--S--[2-(methoxycarbonyl)ethyl]-D-penicillamine allyl ester (0.100 g., 0.19 mmol) in DMSO(1 ml.) at room temperature was added sodium thiomethoxide (0.053 g., 0.762 mmol). After 3.5 hours, the reaction was then acidified with 1N aqueous sodium bisulfate to pH=4 and extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4, and concentrated. The residue was purified on silica eluting with 20% ethyl ethyl acetate in hexane to give N-[4-(4-fluorophenoxy)benzenesulfonyl]-D-penicillamine allyl ester as a colorless oil in 75% yield. 1H--NMR (δ, CDCl3) δ 1.43 (s, 6H), 1.93 (s,1H), 3.82-3.86 (d, 1H, J=11 Hz),4.25-4.38 (m, 2H), 5.23-5.29 (m, 2H), 5.49-5.53 (d, 1H, J=11 Hz), 5.63-5.78 (m,1H), 6.96-7.79 (m, 8H)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified on silica eluting with 20% ethyl ethyl acetate in hexane

Sources & evidence

ORD record
ord-386329124d1f40a0843b3ffbb3dc02b8
Source dataset
uspto-grants-1999_11
Patent number
US05985900

Reaction notes

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