Acetonitrile → HCID 86760667, compound

HRID 2222933Notes

Reaction equation

HRID 2222933 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:6])#[N:2].[C:25](C(N)(S)C)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C.[C:48](#[N:50])C>>[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23][CH2:24][CH2:48][NH:50][C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:6])#[N:2]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 11624809HCID 11624809, compoundHCID 21690497HCID 21690497, compound

Product 1

HCID 86760667HCID 86760667, compound

Procedure

To a solution of trans-N-cyanomethyl-2-(4-methylsulfanylbenzenesulfonylmethyl)-cyclohexanecarboxamide (0.37 g, 1.09 mmol) in acetonitrile (20 mL) were added Boc-aminoethanethiol (0.369 mL, 2.18 mmol) and cesium carbonate (0.713 g, 2.18 mmol). The reaction mixture was heated at reflux for 12 h, and cooled to room temperature. Ethyl acetate (100 mL) was added. The solution was filtered through Celite, concentrated, and purified on a short plug of silica gel (20-50% ethyl acetate/dichloromethane) to yield the desired product. MS [ESI, (M+Na)+] m/z=518 amu.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 12 h
  3. filtrationThe solution was filtered through Celite
  4. concentrationconcentrated
  5. custompurified on a short plug of silica gel (20-50% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-fa395b5dd1de4b0792a2f39da470ae05
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

Loading…