Acetic Acid → (R)-4-(5-tert-butoxycarbonyl-4-methyl-thiazol-2-yl)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid

HRID 908594Notes

Reaction equation

HRID 908594 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:16][N:15]([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)[CH2:14][CH2:13][N:12]1[S:30]([C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:35][CH:34]=1)(=[O:32])=[O:31])=[O:10])C1C=CC=CC=1.C(O)(=O)C>CO.[C].[Pd]>[C:26]([O:25][C:23]([C:19]1[S:18][C:17]([N:15]2[CH2:14][CH2:13][N:12]([S:30]([C:33]3[CH:34]=[CH:35][C:36]([O:39][C:40]([F:43])([F:41])[F:42])=[CH:37][CH:38]=3)(=[O:32])=[O:31])[C@@H:11]([C:9]([OH:10])=[O:8])[CH2:16]2)=[N:21][C:20]=1[CH3:22])=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59703728(R)-4-(5-tert-butoxycarbonyl-4-methyl-thiazol-2-yl)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid benzyl ester

Product 1

HCID 59703741(R)-4-(5-tert-butoxycarbonyl-4-methyl-thiazol-2-yl)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acidYield 79.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of the compound (1.82 g) obtained in Step 5, 10% palladium carbon (250 mg) and acetic acid (4.0 ml) in methanol (50 ml) was stirred under a hydrogen atmosphere (4 atm) at room temperature for 3 hr. The reaction mixture was filtered through celite, and concentrated under reduced pressure. 10% Palladium carbon (1.8 g), acetic acid (4.0 ml) and methanol (50 ml) were added again to the residue, and the mixture was stirred under a hydrogen atmosphere (4 atm) at room temperature for 30 min. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. Toluene was added to the residue, and the mixture was concentrated under reduced pressure (repeated 4 times). The obtained powder was suspended in water, collected by filtration and dried to give the title compound (1.24 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated under reduced pressure
  3. addition10% Palladium carbon (1.8 g), acetic acid (4.0 ml) and methanol (50 ml) were added again to the residue
  4. stirringthe mixture was stirred under a hydrogen atmosphere (4 atm) at room temperature for 30 min
  5. filtrationThe reaction mixture was filtered through celite
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionToluene was added to the residue
  8. concentrationthe mixture was concentrated under reduced pressure (repeated 4 times)
  9. filtrationcollected by filtration
  10. customdried

Sources & evidence

ORD record
ord-894e91e8e0a548fca4e16767ea53ad78
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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