HCID 86728125, compound → HCID 86728126, compound

HRID 627657Notes

Reaction equation

HRID 627657 reaction equation
[CH3:1][C:2]1([CH3:39])[S:7](=[O:9])(=[O:8])[C:6]2([CH3:22])[CH2:10][CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=3[C@@:5]2([CH3:23])[N:4]=[C:3]1[N:24]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]>CCOC(C)=O.CCO.[Pd]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[O:12][CH2:11][CH2:10][C:6]3([CH3:22])[S:7](=[O:8])(=[O:9])[C:2]([CH3:39])([CH3:1])[C:3]([N:24]([C:25]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:31])[C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[N:4][C@:5]3([CH3:23])[C:14]=2[CH:15]=1

Participants

5

Reactant 1

HCID 86728125HCID 86728125, compound

Product 1

HCID 86728126HCID 86728126, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl N-[(11bR)-3,3,4a,11b-tetramethyl-10-nitro-4,4-dioxo-5,6-dihydro-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate (0.076 g, 0.13 mmol) in EtOAc (0.9 ml) and EtOH (0.5 ml) was stirred under hydrogen balloon in the presence of palladium, 10% wt. on activated carbon (0.036 g, 0.033 mmol) for 15 h. The mixture was filtered through the plug of Celite, filter cake was washed with ethyl acetate. The combined filtrate was concentrated to afford crude tert-butyl N-[(11bR)-10-amino-3,3,4a,11b-tetramethyl-4,4-dioxo-5,6-dihydro-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate as mixture of trans and cis diasteromers (˜1:3 ratio) which was used without further purification. m/z (ESI) 560.0 (M+Na)+.

Workup

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

Sources & evidence

ORD record
ord-e5b55f9fb6ed43fdbacdacdcc9ae6160
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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