1-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-pyrrolidine-3-carboxylic acid benzyl ester → HCID 57883821, compound

HRID 253843Notes

Reaction equation

HRID 253843 reaction equation
C([O:8][C:9]([CH:11]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[S:21][C:20]([NH:22][C:23]([N:25]([CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:24])=[N:19][CH:18]=2)[CH2:12]1)=[O:10])C1C=CC=CC=1>[Pd].CO>[CH:32]1([N:25]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:23](=[O:24])[NH:22][C:20]2[S:21][C:17]([CH2:16][N:13]3[CH2:14][CH2:15][CH:11]([C:9]([OH:10])=[O:8])[CH2:12]3)=[CH:18][N:19]=2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

4

Reactant 1

HCID 578839341-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-pyrrolidine-3-carboxylic acid benzyl ester

Product 1

HCID 57883821HCID 57883821, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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.

Workup

  1. customto degas the mixture
  2. custom(24 h)
  3. filtrationAfter filtering
  4. concentrationconcentration
  5. customthe pure acid was obtained by trituration

Sources & evidence

ORD record
ord-83bf0772f40e4cae9e54958ccee9c91f
Source dataset
uspto-grants-2011_01
Patent number
US07872139B2

Reaction notes

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