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

HRID 2384207Notes

Reaction equation

HRID 2384207 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-127d063918e646539bdacfafea35bb69
Source dataset
uspto-grants-2012_09
Patent number
US08263634B2

Reaction notes

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