Reaction #619152

ord-f2d47d0196614aacb8dcb12f26d2bfa3

Reaction equation

O=C(OCc1ccccc1)C1CCN(Cc2cnc(NC(=O)N(C3CCCCC3)C3CCCCC3)s2)C1
1-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-pyrrolidine-3-carboxylic acid benzyl ester
O=C(O)C1CCN(Cc2cnc(NC(=O)N(C3CCCCC3)C3CCCCC3)s2)C1
1-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-pyrrolidine-3-carboxylic acid

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto degas the mixture
  2. 2
    Other(24 h)
  3. 3
    FiltrationAfter filtering
  4. 4
    Concentrationconcentration
  5. 5
    Otherthe pure acid was obtained by trituration

Procedure

1-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-pyrrolidine-3-carboxylic acid benzyl ester (30 mg, 0.057 mmol) was combined with palladium on carbon (20 mg) in MeOH. Vacuum was applied to degas the mixture. The reaction was subjected to hydrogen and vigorous stirring until no ester could be detected (24 h). After filtering and concentration, the pure acid was obtained by trituration.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE045183E1uspto-grants-2014_10