1-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-pyrrolidine-2(R)-carboxylic acid benzyl ester → 1-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-yl-methyl]-pyrrolidine-2(R)-carboxylic acid

HRID 2263778Notes

Reaction equation

HRID 2263778 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[CH2:16][C:17]1[S:21][C:20]([NH:22][C:23]([N:25]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:24])=[N:19][CH:18]=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:12]3[CH2:13][CH2:14][CH2:15][C@@H:11]3[C:9]([OH:10])=[O:8])=[CH:18][N:19]=2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

4

Reactant 1

HCID 578836361-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-pyrrolidine-2(R)-carboxylic acid benzyl ester

Product 1

HCID 578838911-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-yl-methyl]-pyrrolidine-2(R)-carboxylic acidYield 84.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-[2-(3,3-Dicyclohexyl-ureido)-thiazol-5-ylmethyl]-pyrrolidine-2(R)-carboxylic acid benzyl ester (50 mg, 0.095 mmol) was combined with palladium on carbon (25 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 (36 h). After filtering and concentration, 35 mg (84%) pure acid was obtained by trituration.

Workup

  1. customto degas the mixture
  2. custom(36 h)
  3. filtrationAfter filtering
  4. concentrationconcentration

Sources & evidence

ORD record
ord-0f75f3bdb7dd420d83f6e3e8f71bab55
Source dataset
uspto-grants-2010_12
Patent number
US07851636B2

Reaction notes

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