Benzyl mercaptan → HCID 10310600, compound

HRID 2222944Notes

Reaction equation

HRID 2222944 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([CH2:9][NH:10][C:11]([C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[CH2:19][S:20]([C:23]1[CH:34]=[CH:33][C:26]([CH2:27]OS(C)(=O)=O)=[CH:25][CH:24]=1)(=[O:22])=[O:21])=[O:12])#[N:8].[CH2:35]([SH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CC(C)=O>[C:7]([CH2:9][NH:10][C:11]([C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[CH2:19][S:20]([C:23]1[CH:34]=[CH:33][C:26]([CH2:27][S:42][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:25][CH:24]=1)(=[O:21])=[O:22])=[O:12])#[N:8]

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 10796Cesium carbonateHCID 131726870HCID 131726870, compound

Product 1

HCID 10310600HCID 10310600, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

Cesium carbonate (0.114 g, 0.35 mmol) was added to a solution of trans-methanesulfonic acid 4-[2-(cyanomethylcarbamoyl)-cyclohexylmethanesulfonyl]-benzyl ester (0.150 g, 0.35 mmol) and benzyl mercaptan (0.041 mL, 0.35 mmol) in acetone (4 mL). The reaction mixture was stirred overnight at 50° C. The solids were removed by filtration and washed with warm acetone. The combined filtrates were concentrated by rotary evaporation. Purification of the residue by silica gel chromatography using a gradient of 0%-20% ethyl acetate in dichloromethane yielded the title compound as a white solid.

Workup

  1. customThe solids were removed by filtration
  2. washwashed with warm acetone
  3. concentrationThe combined filtrates were concentrated by rotary evaporation
  4. customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-907a344c477e4fa884ded2364af78451
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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