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

HRID 531970Notes

Reaction equation

HRID 531970 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-f2d47d0196614aacb8dcb12f26d2bfa3
Source dataset
uspto-grants-2014_10
Patent number
USRE045183E1

Reaction notes

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