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

HRID 2263784Notes

Reaction equation

HRID 2263784 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-ab2963cf04824ee39036873fe73b9e54
Source dataset
uspto-grants-2010_12
Patent number
US07851636B2

Reaction notes

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