Potassium Carbonate → HCID 54562908, compound

HRID 2288006Notes

Reaction equation

HRID 2288006 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].CN(C)C(=O)C.[CH:32]1([SH:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>O>[CH:32]1([S:38][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 15290CyclohexanethiolHCID 31374DimethylacetamideHCID 22713394HCID 22713394, compound

Product 1

HCID 54562908HCID 54562908, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The N-[(4-flourophenyl)sulphonyl]glycine, 1,1-dimethylethyl ester from Example 5a (4.5 mmol, 1.30 g) was combined with dried 325 mesh K2CO3 (5.0 mmol, 0.69 g) and N,N-dimethylacetamide (4.5 mL). Cyclohexyl mercaptan (5 mmol, 0.61 mL) was added, and the mixture was stirred under argon at 60° C. for 40 hours. Water (50 mL) was added, and the mixture was extracted with ethyl acetate (125 mL). The organic phase was dried using magnesium sulphate, filtered through silica, and concentrated. The N-[[4-(cyclohexyl-thio)phenyl]sulfonyl]glycine, 1,1-dimethylethyl ester, a white solid (528 mg), was obtained following chromatography eluting with hexane:ethyl acetate (4:1). NMR indicated the presence of about 20% starting material after chromatography, but the mixture was used as is in the next step. The structure was confirmed spectroscopically.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (125 mL)
  2. customThe organic phase was dried
  3. filtrationfiltered through silica
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7362dade397a43ca948cddb55367edfb
Source dataset
uspto-grants-2000_07
Patent number
US06087359

Reaction notes

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