HCID 67376231, compound → HCID 86608784, compound

HRID 1677599Notes

Reaction equation

HRID 1677599 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[CH:9][CH:8]=1)=[CH2:6])[CH3:2].[C:25]([OH:28])(=[S:27])[CH3:26]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:24])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[CH:9][CH:8]=1)[CH2:6][S:27][C:25](=[O:28])[CH3:26])[CH3:2]

Participants

4

Reactant 2

HCID 67376231HCID 67376231, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86608784HCID 86608784, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-(4-(benzyloxycarbonylamino)phenyl)prop-2-enoic acid ethyl ester (2.2 g, 7.55 mmol) and thioacetic acid (5 mL) in 10 mL of chloroform was heated for 18 hours. The reaction mixture was evaporated in vacuo and purified by flash chromatography through silica gel (5/1 hexanes/ethyl acetate) to afford 2-(4-(benzyloxycarbonylamino)phenyl)-3-(acetylthio)propanoic acid ethyl ester, 0.22 g (8%) as an oil.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. custompurified by flash chromatography through silica gel (5/1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-2b46806bd7134be0b9026e8d95101191
Source dataset
uspto-grants-2011_08
Patent number
US08008325B2

Reaction notes

Loading…