HCID 90308599, compound → HCID 90308595, compound

HRID 627667Notes

Reaction equation

HRID 627667 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]>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

4

Reactant 1

HCID 90308599HCID 90308599, compound

Product 1

HCID 90308595HCID 90308595, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl-N-((4aR,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 (390 mg, 0.707 mmol) in THF (5 ml) was hydrogenated using a balloon in the presence of palladium (10% wt.) on activated carbon (150 mg, 0.141 mmol) for 1.5 h. The mixture was filtered through pad of celite, filter cake was washed with THF, filtrate was concentrated to afford tert-butyl-N-((4aR,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 (340 mg, 0.652 mmol, 92% yield) which was used in the next step without purification. LC/MS (ESI+) m/z=522 (M+H).

Workup

  1. customfor 1.5 h
  2. filtrationThe mixture was filtered through pad of celite
  3. filtrationfilter cake
  4. washwas washed with THF, filtrate
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-1b5b5ca7457c492d872da39bfd2979cc
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

Loading…