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 531965Notes

Reaction equation

HRID 531965 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-42d640add8a04c2f836af2fad21ff0c2
Source dataset
uspto-grants-2014_10
Patent number
USRE045183E1

Reaction notes

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