HCID 90301249, compound → HCID 90301277, compound

HRID 627673Notes

Reaction equation

HRID 627673 reaction equation
[CH3:1][C:2]1([CH3:40])[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[N:25]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29]>CCOC(C)=O.CO.[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]([CH3:40])([CH3:1])[C:3]([N:25]([C:26]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:32])[C:33](=[O:34])[O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[N:4][C@:5]3([CH3:24])[C:14]=2[CH:15]=1

Participants

5

Reactant 1

HCID 90301249HCID 90301249, compound

Product 1

HCID 90301277HCID 90301277, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl N-[(4aS,11bR)-3,3,6,6,11b-pentamethyl-10-nitro-4,4-dioxo-4a,5-dihydro-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate (70 mg, 0.120 mmol) (Prepared following the procedure for Intermediate 31 (trans), Step 1 and 2) and 10% Pd/C (38.6 mg, 0.036 mmol) in EtOAc (1.1 mL) and MeOH (1.1 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 (66 mg, 0.120 mmol, 100% yield) as a white foam. MS m/z=574.3 (M+Na).

Workup

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

Sources & evidence

ORD record
ord-819b57916c4e4520938a6d192feb0352
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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