Dimethyl Sulfoxide → HCID 86585077, compound

HRID 1264425Notes

Reaction equation

HRID 1264425 reaction equation
COC1C=CC(C[S:8][C@H:9]2[CH2:13][N:12]([S:14]([C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=3)(=[O:16])=[O:15])[C@H:11]([C:27]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[O:28])[CH2:10]2)=CC=1.C[Si](Cl)(C)C.CS(C)=O.C([O-])([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[K+].[K+].C(S)[C@@H](O)[C@H](O)CS.OS([O-])(=O)=O.[K+]>C(O)(C(F)(F)F)=O.CO>[SH:8][C@H:9]1[CH2:13][N:12]([S:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)(=[O:16])=[O:15])[C@H:11]([C:27]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)=[O:28])[CH2:10]1

Participants

10

Reactant 7

HCID 679Dimethyl SulfoxideHCID 6397ChlorotrimethylsilaneHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 446094D-1,4-DithiothreitolHCID 516920Potassium bisulfateHCID 70001572HCID 70001572, compound

Product 1

HCID 86585077HCID 86585077, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

140 mg (0.26 mmol) (2S,4R)-[4-(4-methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanone in 2 ml TFA were treated with 0.45 ml (6 mmol) trimethylsilyl chloride and 0.3 ml (6 mmol) DMSO for 2 h at RT, added to a sat. solution of Na2CO3 and extracted with EtOAc, washed with brine and dried. The crude product was dissolved in 6 ml acetonitrile, a sat. solution of K2CO3 in MeOH and 100 mg (0.65 mmol) DTT were added. The solution was stirred at RT for 1.5 h, the solution was acidified with 1M aq KHSO4 and the inorganic phase was extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated. Flash chromatography yielded 89.5 mg (81%) (2S,4R)-[4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanone as light yellow solid, MS: 292 (M-C5H9O)+, 135 (C5H9O)+.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. customdried
  4. dissolutionThe crude product was dissolved in 6 ml acetonitrile
  5. extractionthe inorganic phase was extracted with EtOAc
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-b37c244255644700ad77b9a93a2f9d22
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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