HCID 58376060, compound → HCID 58376590, compound

HRID 1942530Notes

Reaction equation

HRID 1942530 reaction equation
C(OC([NH:11][CH2:12][CH2:13][N:14]1[C:19]2[CH:20]=[C:21]([C:25]([N:27]([CH:41]([CH3:43])[CH3:42])[C@@H:28]3[CH2:33][CH2:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29]3)=[O:26])[C:22]([CH3:24])=[CH:23][C:18]=2[S:17][C:16]([CH3:45])([CH3:44])[C:15]1=[O:46])=O)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:11][CH2:12][CH2:13][N:14]1[C:19]2[CH:20]=[C:21]([C:25]([N:27]([CH:41]([CH3:42])[CH3:43])[C@@H:28]3[CH2:33][CH2:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[CH2:29]3)=[O:26])[C:22]([CH3:24])=[CH:23][C:18]=2[S:17][C:16]([CH3:44])([CH3:45])[C:15]1=[O:46]

Participants

4

Reactant 1

HCID 58376060HCID 58376060, compound

Product 1

HCID 58376590HCID 58376590, compoundYield 116.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl (3R)-3-[{[4-(2-{[(benzyloxy)carbonyl]amino}ethyl)-2,2,7-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-6-yl]carbonyl}(isopropyl)amino]piperidine-1-carboxylate (1.4 g) was dissolved in methanol (11 ml), and thereto was added a 20% palladium hydroxide/carbon (50% wet.) (0.7 g) under hydrogen atmosphere, and the mixture was vigorously stirred at room temperature for 3 hours. After the reaction was complete, the reaction mixture was filtered on celite, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: chloroform/methanol=98/2˜92/8) to give the title compound (1.3 g).

Workup

  1. filtrationthe reaction mixture was filtered on celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-0aa554064c214d1aa9edde6f3e5e02a1
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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