HCID 131735336, compound → HCID 131735335, compound

HRID 627736Notes

Reaction equation

HRID 627736 reaction equation
[F:1][C:2]12[CH2:12][CH2:11][O:10][C:9]3[CH:13]=[CH:14][C:15]([N+:17]([O-])=O)=[CH:16][C:8]=3[C@@:7]1([CH3:20])[N:6]=[C:5]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:4]([CH3:30])([CH3:29])[S:3]2(=[O:32])=[O:31]>CCOC(C)=O.CO.[Pd]>[NH2:17][C:15]1[CH:14]=[CH:13][C:9]2[O:10][CH2:11][CH2:12][C:2]3([F:1])[S:3](=[O:32])(=[O:31])[C:4]([CH3:30])([CH3:29])[C:5]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[N:6][C@:7]3([CH3:20])[C:8]=2[CH:16]=1

Participants

5

Reactant 1

HCID 131735336HCID 131735336, compound

Product 1

HCID 131735335HCID 131735335, compoundYield 84.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A round bottom flask was charged with Pd/C (0.020 g, 0.019 mmol) and put under a nitrogen atmosphere. A solution of tert-butyl ((11bR)-4a-fluoro-3,3,11b-trimethyl-10-nitro-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (0.090 g, 0.191 mmol) in EtOAc (477 μl) and MeOH (477 μl) was added via syringe and the flask was evacuated and filled with hydrogen. The mixture was stirred at RT under hydrogen atmosphere for 17 hours. The mixture was filtered through Celite and washed with EtOAc and the filtrate was concentrated to yield tert-butyl ((11bR)-10-amino-4a-fluoro-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (0.071 mg, 0.161 mmol, 84% yield) as a light yellow solid. LC/MS (ESI+) m/z=442.3.

Workup

  1. customthe flask was evacuated
  2. additionfilled with hydrogen
  3. filtrationThe mixture was filtered through Celite
  4. washwashed with EtOAc
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-106204ba33314e6d82fdddd568589c44
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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