HCID 72347756, compound → HCID 86617854, compound

HRID 552893Notes

Reaction equation

HRID 552893 reaction equation
[CH3:1][C:2]1([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:20][C:19]2[CH:21]=[C:15]([CH:16]=[CH:17][CH:18]=2)[CH2:14][CH:13]=[CH:12][CH2:11][C:10]2=[CH:22][C:6](=[CH:7][C:8]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])=[N:9]2)[CH2:5][O:4][C:3]1=[O:29]>C1COCC1.[Pd]>[CH3:1][C:2]1([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:20][C:19]2[CH:21]=[C:15]([CH:16]=[CH:17][CH:18]=2)[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[CH:22][C:6](=[CH:7][C:8]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])=[N:9]2)[CH2:5][O:4][C:3]1=[O:29]

Participants

4

Reactant 1

HCID 72347756HCID 72347756, compound

Product 1

HCID 86617854HCID 86617854, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [(3EZ)-14-methyl-8-[methyl(methylsulfonyl)amino]-13-oxo-12-oxa-7-azatricyclo[14.3.1.16,10]henicosa-1(20),3,6(21),7,9,16,18-heptaen-14-yl]carbamate (22.5 mg, 0.042 mmol) (Intermediate V.11.c.1) in degassed THF (2.5 mL) was added palladium on carbon (10%, 3 mg). The reaction was stirred under a hydrogen atmosphere (1 atm) for 1 h and filtered through celite. Concentration gave tert-butyl [14-methyl-8-[methyl(methylsulfonyl)amino]-13-oxo-12-oxa-7-azatricyclo[14.3.1.16,10]henicosa-1(20),6(21),7,9,16,18-hexaen-14-yl]carbamate. MS: 532.0 (M+1) ES+

Workup

  1. filtrationfiltered through celite
  2. concentrationConcentration

Sources & evidence

ORD record
ord-8eb3cfc239404a788e3935ca8bdcf454
Source dataset
uspto-grants-2011_05
Patent number
US07951949B2

Reaction notes

Loading…