3-Thiocresol → HCID 53937076, compound

HRID 2287997Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([SH:30])[CH:25]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:23][C:24]1[CH:25]=[C:26]([S:30][C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N-[(4-fluorophenyl)-sulfonyl]-D-valine, 1,1-dimethylethyl ester, from Example 1b (3.0 g, 9.06 mmol) in 35 mL DMF was added m-thiocresol (3.23 mL, 27.2 mmol) and powdered K2CO3 (3.76 g, 27.2 mmol). The mixture was heated to 70° C. for 20 hours. After cooling to room temperature, the solution is washed with H2O (4×100 mL), and sat'd NaCl (2×100 mL), and dried over Mg2SO4. After concentration in vacuo, the residue was purified by flash chromatography (10:90 EtOAc/hexane) to afford N-[[4-[(3-methylphenyl)thio]phenyl]sulfonyl]-D-valine, 1,1-dimethylethyl ester, as a white solid (3.95 g, quantitative yield): MS MH+ calc'd for C22H29NO4S2 : 436, found: 436. Anal. calc'd for C22H29NO4S2 : C, 60.66; H, 6.71; N, 3.22; Found: C, 60.57; H, 6.47; N, 3.14.

Workup

temperatureAfter cooling to room temperature
washthe solution is washed with H2O (4×100 mL), and sat'd NaCl (2×100 mL)
dry with materialdried over Mg2SO4
concentrationAfter concentration in vacuo
customthe residue was purified by flash chromatography (10:90 EtOAc/hexane)

Sources & evidence

ORD record: ord-c676397e81ba467e87a89ed371dd22fd
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06087359

Reaction notes

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