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 2384201Notes

Reaction equation

HRID 2384201 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-38abed24698b4f84904d15f61285bc67
Source dataset
uspto-grants-2012_09
Patent number
US08263634B2

Reaction notes

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