Nitrogen → HCID 90308654, compound

HRID 627738Notes

Reaction equation

HRID 627738 reaction equation
[CH3:1][C:2]1([CH3:33])[S:7](=[O:9])(=[O:8])[C@@H:6]2[CH2:10][C:11]([CH3:23])([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([CH3:24])[N:4]=[C:3]1[NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].N#N.[H][H]>C1COCC1.[Pd]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[O:12][C:11]([CH3:23])([CH3:22])[CH2:10][C@H:6]3[S:7](=[O:8])(=[O:9])[C:2]([CH3:33])([CH3:1])[C:3]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[N:4][C@:5]3([CH3:24])[C:14]=2[CH:15]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 131735337HCID 131735337, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 90308654HCID 90308654, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

Solution of tert-butyl ((4aR,11bR)-3,3,6,6,11b-pentamethyl-10-nitro-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (56 mg, 0.116 mmol) in THF (1.1 ml) was purged with N2, and hydrogenated under hydrogen balloon in the presence of palladium 10 wt. % Pd on activated carbon (37.1 mg, 0.035 mmol) for 4.5 h. The mixture was filtered through the plug of Celite, and the filter cake was washed with ethyl acetate. The combined filtrate was concentrated to afford the crude tert-butyl ((4aR,11bR)-10-amino-3,3,6,6,11b-pentamethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate which was used for next step directly. MS m/z=452.1 (M+H).

Workup

  1. filtrationThe mixture was filtered through the plug of Celite
  2. washthe filter cake was washed with ethyl acetate
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-385e5939a0314c9ea1a619a4f0815a95
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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