HCID 86728112, compound → HCID 86728113, compound

HRID 627644Notes

Reaction equation

HRID 627644 reaction equation
[F:1][CH2:2][C@@:3]12[C:32]3[CH:33]=[C:34]([N+:37]([O-])=O)[CH:35]=[CH:36][C:31]=3[O:30][CH2:29][CH2:28][C@@H:4]1[S:5](=[O:27])(=[O:26])[C:6]([CH3:25])([CH3:24])[C:7]([N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:8]2>CCOC(C)=O.CCO.[Pd]>[F:1][CH2:2][C@@:3]12[C:32]3[CH:33]=[C:34]([NH2:37])[CH:35]=[CH:36][C:31]=3[O:30][CH2:29][CH2:28][C@@H:4]1[S:5](=[O:26])(=[O:27])[C:6]([CH3:24])([CH3:25])[C:7]([N:9]([C:10]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:16])[C:17](=[O:18])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[N:8]2

Participants

5

Reactant 1

HCID 86728112HCID 86728112, compound

Product 1

HCID 86728113HCID 86728113, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl N-[(4aS,11bS)-11b-(fluoromethyl)-3,3-dimethyl-10-nitro-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate (647 mg, 1.13 mmol) in EtOAc (15 mL) and EtOH (5 mL) was hydrogenated at 1 atm. in the presence of palladium (10% wt. on activated carbon) (120 mg, 1.13 mmol) for 5 h at RT. The mixture was filtered through the pad of celite and washed 3 times with EtOAc. The filtrate was concentrated in vacuo to give tert-butyl N-[(4aS,11bS)-11b-(fluoromethyl)-3,3-dimethyl-10-amino-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate (613 mg, 100%) as a white solid. LC/MS (ESI+) m/z=564 (M+Na).

Workup

  1. filtrationThe mixture was filtered through the pad of celite
  2. washwashed 3 times with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b4c2cf38a8c743e6af5ee33909a3295c
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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