HCID 90308594, compound → HCID 90301520, compound

HRID 627665Notes

Reaction equation

HRID 627665 reaction equation
[C:1]([O:5][C:6](=[O:38])[N:7]([C:15]1[C:20]([CH3:22])([CH3:21])[S:19](=[O:24])(=[O:23])[C@H:18]2[CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][C:29]=3[C@@:17]2([CH3:37])[N:16]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].[H][H]>C1COCC1.[Pd]>[C:1]([O:5][C:6](=[O:38])[N:7]([C:15]1[C:20]([CH3:22])([CH3:21])[S:19](=[O:24])(=[O:23])[C@H:18]2[CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][C:29]=3[C@@:17]2([CH3:37])[N:16]=1)[C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 90308594HCID 90308594, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 90301520HCID 90301520, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl-N-((4aS,11bR)-10-nitro-3,3,11b-trimethyl-4,4-dioxido-3,4a,5,6,7,11b-hexahydrobenzo[3,4]cyclohepta[1,2-b][1,4]thiazin-2-yl)-N-tert-butoxycarbonyl-carbamate (125 mg, 0.227 mmol) in THF (2 ml) was hydrogenated in the presence of palladium (10% wt.) on activated carbon (48.2 mg, 0.045 mmol) for 1 h (hydrogen balloon). The mixture was filtered through plug of celite, filter cake was washed with EtOAc, filtrate was concentrated to afford tert-butyl-N-((4aS,11bR)-10-amino-3,3,11b-trimethyl-4,4-dioxido-3,4a,5,6,7,11b-hexahydrobenzo[3,4]cyclohepta[1,2-b][1,4]thiazin-2-yl)-N-tert-butoxycarbonyl-carbamate (116 mg, 0.222 mmol, 98% yield), which was used without further purification. LC/MS (ESI+) m/z=522 (M+H).

Workup

  1. filtrationThe mixture was filtered through plug of celite
  2. filtrationfilter cake
  3. washwas washed with EtOAc, filtrate
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-37c1f07c92b44cf19fa3f0257a1946ed
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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