Reaction #61704

ord-26c34aec773746eaaedbc15bbd53c9eb

Reaction equation

C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(Cc2nccs2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O
tert-butyl(2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](1,3-thiazol-2-ylmethyl)amino]-2-oxopyrrolidin-1-yl}propanoate
O=C(O)C(F)(F)F
trifluoroacetic acid
→
C[C@@H](C(=O)O)N1CC[C@H](N(Cc2nccs2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O
title compound
Yield 70.5%
C[C@@H](C(=O)O)N1CC[C@H](N(Cc2nccs2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O
(2S)-2-{(3S)-3-[[(6-Chloro-2-naphthyl)sulfonyl](1,3-thiazol-2-ylmethyl)amino]-2-oxopyrrolidin-1-yl}propanoic acid
Yield 70.5%

Reactants

C[C@@H](C(=O)OC(C)(C)C)N1CC[C@H](N(Cc2nccs2)S(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O
tert-butyl(2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](1,3-thiazol-2-ylmethyl)amino]-2-oxopyrrolidin-1-yl}propanoate
O=C(O)C(F)(F)F
trifluoroacetic acid

Reagents

None

Solvents

ClCCl
DCM

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe solution was then concentrated under reduced pressure

Procedure

A solution of tert-butyl(2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](1,3-thiazol-2-ylmethyl)amino]-2-oxopyrrolidin-1-yl}propanoate (0.03 g) in DCM (1 ml) was treated with trifluoroacetic acid (1ml) and stirred at room temperature for 1 h. The solution was then concentrated under reduced pressure to give the title compound (0.019 g) as a colourless solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07429587B2uspto-grants-2008_09