Methanol → HCID 86728133, compound

HRID 627670Notes

Reaction equation

HRID 627670 reaction equation
[CH3:1][C:2]1([CH3:39])[S:7](=[O:9])(=[O:8])[C@@H:6]2[CH2:10][C@H:11]([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([CH3:23])[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].CO>[Pd].C(OCC)(=O)C>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[O:12][C@@H:11]([CH3:22])[CH2:10][C@H:6]3[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 2

HCID 887MethanolHCID 86728131HCID 86728131, compound

Product 1

HCID 86728133HCID 86728133, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl N-[(4aR,6S,11bR)-3,3,6,11b-tetramethyl-10-nitro-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate (7.3 g, 12.86 mmol) and palladium on carbon (10%), wet (1 g, 0.470 mmol) were combined in ethyl acetate (60 ml) with 5 ml of MeOH under hydrogen atmosphere and stirred at room temp for 1 h. The solution was filtered thru celite, the Pd solids were washed with DCM and MeOH, then the organics were concentrated to afford tert-butyl N-[(4aR,6S,11bR)-10-amino-3,3,6,11b-tetramethyl-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate (6.5 g, 12.09 mmol, 94% yield) as a white solid. MS m/z=560 [M+Na].

Workup

  1. filtrationThe solution was filtered thru celite
  2. washthe Pd solids were washed with DCM and MeOH
  3. concentrationthe organics were concentrated

Sources & evidence

ORD record
ord-8273ae5d64b7449ebe66e28a8b7a53e1
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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