HCID 121266513, compound → HCID 90308622, compound

HRID 627653Notes

Reaction equation

HRID 627653 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]([N:21]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:4]([CH3:37])([CH3:36])[S:3]2(=[O:39])=[O:38]>C1COCC1>[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:39])(=[O:38])[C:4]([CH3:37])([CH3:36])[C:5]([N:21]([C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])[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

3

Reactant 1

HCID 121266513HCID 121266513, compound

Product 1

HCID 90308622HCID 90308622, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl N-[(4aR,11bR)-4a-fluoro-3,3,11b-trimethyl-10-nitro-4,4-dioxo-5,6-dihydro-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate (490 mg, 0.857 mmol) and pd/c (274 mg, 0.257 mmol) in THF (5.7 mL) was stirred under hydrogen atmosphere for 16 hours. The mixture was passed through a celite cake and rinsed with ethyl acetate and ethanol. The filtrate was concentrated in vacuo to afford the title compound (460 mg, 0.850 mmol, 99% yield) as a white foam. MS m/z=564.2 (M+Na).

Workup

  1. washrinsed with ethyl acetate and ethanol
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-93fb1823e43b45be97c97b02b87c9a97
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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