HCID 67376231, compound → HCID 86608784, compound

HRID 490923Notes

Reaction equation

HRID 490923 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-05734a6f77864d0f8d0772c1467282b5
Source dataset
uspto-grants-2009_05
Patent number
US07528173B2

Reaction notes

Loading…