HCID 131735328, compound → HCID 90307385, compound

HRID 627659Notes

Reaction equation

HRID 627659 reaction equation
[CH3:1][C:2]1([CH3:32])[S:7](=[O:9])(=[O:8])[C@@H:6]2[CH2:10][C@@H:11]([CH3:22])[O:12][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=3[C@@:5]2([CH3:23])[N:4]=[C:3]1[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]>C1COCC1.[Pd]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[O:12][C@H:11]([CH3:22])[CH2:10][C@H:6]3[S:7](=[O:8])(=[O:9])[C:2]([CH3:32])([CH3:1])[C:3]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[N:4][C@:5]3([CH3:23])[C:14]=2[CH:15]=1

Participants

4

Reactant 1

HCID 131735328HCID 131735328, compound

Product 1

HCID 90307385HCID 90307385, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl ((4aR,6R,11bR)-3,3,6,11b-tetramethyl-10-nitro-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (50 mg, 0.107 mmol) in THF (1 ml) was hydrogenated under hydrogen balloon in the presence of palladium 10 wt. % on activated carbon (34.1 mg, 0.032 mmol) for 1.5 h. The mixture was filtered through the plug of Celite, filter cake was washed with ethyl acetate. The combined filtrate was concentrated to afford crude tert-butyl ((4aR,6R,11bR)-10-amino-3,3,6,11b-tetramethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (46 mg, 0.105 mmol, 98% yield) which was used without further purification. MS m/z=438.3 (M+H).

Workup

  1. customfor 1.5 h
  2. filtrationThe mixture was filtered through the plug of Celite
  3. filtrationfilter cake
  4. washwas washed with ethyl acetate
  5. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-5c8f879617074ec7b192e0a9e7f1e8d8
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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