(R)-4-(5-tert-butoxycarbonyl-4-methyl-thiazol-2-yl)-2-(4-propyl-benzylcarbamoyl)-piperazine-1-carboxylic acid benzyl ester → 4-methyl-2-[(R)-3-(4-propyl-benzylcarbamoyl)-piperazin-1-yl]-thiazole-5-carboxylic acid tert-butyl ester

HRID 908600Notes

Reaction equation

HRID 908600 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[S:18][C:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:20]([CH3:22])[N:21]=2)[CH2:13][C@@H:12]1[C:30](=[O:42])[NH:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH3:41])=[CH:35][CH:34]=1)=O)C1C=CC=CC=1>CO.[C].[Pd]>[C:26]([O:25][C:23]([C:19]1[S:18][C:17]([N:14]2[CH2:15][CH2:16][NH:11][C@@H:12]([C:30](=[O:42])[NH:31][CH2:32][C:33]3[CH:34]=[CH:35][C:36]([CH2:39][CH2:40][CH3:41])=[CH:37][CH:38]=3)[CH2:13]2)=[N:21][C:20]=1[CH3:22])=[O:24])([CH3:28])([CH3:29])[CH3:27]

Participants

4

Reactant 1

HCID 59703739(R)-4-(5-tert-butoxycarbonyl-4-methyl-thiazol-2-yl)-2-(4-propyl-benzylcarbamoyl)-piperazine-1-carboxylic acid benzyl ester

Product 1

HCID 597038424-methyl-2-[(R)-3-(4-propyl-benzylcarbamoyl)-piperazin-1-yl]-thiazole-5-carboxylic acid tert-butyl esterYield 88.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of the compound (1.00 g) obtained in Step 5 and 7.5% palladium carbon (1.0 g) in methanol (15 ml) was stirred under a hydrogen atmosphere (5 atm) at room temperature for 4 hr. The reaction mixture was filtered through celite, and concentrated under reduced pressure. 10% Palladium carbon (500 mg) and methanol (15 ml) were added again to the residue, and the mixture was stirred under a hydrogen atmosphere (5 atm) at room temperature for 6 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (3%-5% methanol/chloroform) to give the title compound (688 mg).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated under reduced pressure
  3. addition10% Palladium carbon (500 mg) and methanol (15 ml) were added again to the residue
  4. stirringthe mixture was stirred under a hydrogen atmosphere (5 atm) at room temperature for 6 hr
  5. filtrationThe reaction mixture was filtered through celite
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by column chromatography (3%-5% methanol/chloroform)

Sources & evidence

ORD record
ord-ce34f5aeb3d14afbb906a0e7f947f29b
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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