HCID 21072803, compound → HCID 21072804, compound

HRID 1372926Notes

Reaction equation

HRID 1372926 reaction equation
[OH:1][CH:2]([C:23]1[C:32]2[O:31][CH2:30][C:29](=[O:33])[NH:28][C:27]=2[CH:26]=[C:25]([OH:34])[CH:24]=1)[CH2:3][NH:4][C:5]1([CH2:8][CH2:9][N:10]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13]([CH3:21])([CH3:20])[O:12][CH:11]2[OH:22])[CH2:7][CH2:6]1.[H][H]>CO.[Pd]>[OH:1][CH:2]([C:23]1[C:32]2[O:31][CH2:30][C:29](=[O:33])[NH:28][C:27]=2[CH:26]=[C:25]([OH:34])[CH:24]=1)[CH2:3][NH:4][C:5]1([CH2:8][CH2:9][N:10]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13]([CH3:21])([CH3:20])[O:12][C:11]2=[O:22])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 21072803HCID 21072803, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21072804HCID 21072804, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(2-{1-[2-hydroxy-2-(6-hydroxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-ethylamino]-cyclopropyl}-ethyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-ol 590 mg (1.06 mmol) 1-(2-{1-[2-(6-benzyloxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-2-hydroxy-ethylamino]-cyclopropyl}-ethyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one are dissolved in 30 mL methanol and hydrogenated in the presence of palladium on charcoal (10%) at ambient temperature and 3 bar hydrogen pressure. Yield: 180 mg (36%); mass spectroscopy: [M+H]+=468.

Sources & evidence

ORD record
ord-99c6fb74d7e542d6b84d05a7c54e1aed
Source dataset
uspto-grants-2007_01
Patent number
US07160882B2

Reaction notes

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