2-Acetylsulfanylmethyl-3-(cis4-tert-butoxycarbonylamino-cyclopent-2-enyl)-propionic acid ethyl ester → 3-(Cis4-amino-cyclopent-2-enyl)-2-mercaptomethyl-propionic acid

HRID 1789903Notes

Reaction equation

HRID 1789903 reaction equation
C([O:3][C:4](=[O:25])[CH:5]([CH2:20][S:21]C(=O)C)[CH2:6][C@H:7]1[CH2:11][C@@H:10]([NH:12]C(OC(C)(C)C)=O)[CH:9]=[CH:8]1)C>Cl>[NH2:12][C@@H:10]1[CH2:11][C@H:7]([CH2:6][CH:5]([CH2:20][SH:21])[C:4]([OH:25])=[O:3])[CH:8]=[CH:9]1

Participants

3

Reactant 1

HCID 867601212-Acetylsulfanylmethyl-3-(cis4-tert-butoxycarbonylamino-cyclopent-2-enyl)-propionic acid ethyl ester

Product 1

HCID 867601223-(Cis4-amino-cyclopent-2-enyl)-2-mercaptomethyl-propionic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-acetylsulfanylmethyl-3-(cis4-tert-butoxycarbonylamino-cyclopent-2-enyl)-propionic acid ethyl ester (86 mg, 0.23 mmol) in concentrated HCl (5 mL) was refluxed under argon for 1 h. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to afford a diasteromeric mixture of the title compound as the hydrochloride salt (65 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto afford

Sources & evidence

ORD record
ord-59a07de6b36443fbb563d0cae51904a6
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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