Diisopropylethylamine → S-methyl--N--[4-(phenoxy)benzenesulfonyl]-D-penicillamine methyl ester

HRID 1602985Notes

Reaction equation

HRID 1602985 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C@@H:4]([C:6]([S:9][CH3:10])([CH3:8])[CH3:7])[NH2:5].C(N(C(C)C)CC)(C)C.[O:21]([C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl>[CH3:1][O:2][C:3](=[O:11])[C@@H:4]([C:6]([S:9][CH3:10])([CH3:8])[CH3:7])[NH:5][S:34]([C:31]1[CH:30]=[CH:29][C:28]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:33][CH:32]=1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27947564-Phenoxybenzene-1-sulfonyl chlorideHCID 18395020S-methyl-D-penicillamine methyl ester

Product 1

HCID 57188101S-methyl--N--[4-(phenoxy)benzenesulfonyl]-D-penicillamine methyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of S-methyl-D-penicillamine methyl ester (0.160 g., 0.904 mmol) and diisopropylethylamine (0.172 mL, 0.99 mmol) in dichloromethane (3 mL) was added 4-phenoxybenzenesulfonyl chloride (0.304 g, 1.13 mmol) via solid addition funnel. After 2.5 hours at room temperature, the solution was concentrated and the residue was purified on silica, eluting with 20% ethyl acetate in hexane, to give S-methyl--N--[4-(phenoxy)benzenesulfonyl]-D-penicillamine methyl ester as a white solid in 87% yield: 1H NMR (CDCl3) δ 1.31 (s, 3H), 1.37 (s, 3H), 1.96 (s,3H), 3.48 (s, 3H), 3.79 (d, 1H, J=9 Hz), 5.34 (d, 1H, J=10 Hz), 6.99-7.79 (m, 9H); FAB HRMS: expected (M+Na)=432.0915, found (M+Na)=432.0907.

Workup

  1. additionvia solid addition funnel
  2. concentrationthe solution was concentrated
  3. customthe residue was purified on silica
  4. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-fa44eb27555c4bbe979d7e1d12045892
Source dataset
uspto-grants-1999_11
Patent number
US05985900

Reaction notes

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