Ammonia → (R)-3-(2-(2-(tert-Butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde

HRID 1689519Notes

Reaction equation

HRID 1689519 reaction equation
C(=O)([O:7][C:8]1[CH:9]=[CH:10][C:11]([C@@H:19]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH2:20][NH:21][C:22]([CH3:33])([CH3:32])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=[O:31])[CH:25]=2)=[C:12]2[C:17]=1[NH:16][C:15](=[O:18])[CH:14]=[CH:13]2)OC(C)(C)C.N>CO>[Si:35]([O:34][C@H:19]([C:11]1[CH:10]=[CH:9][C:8]([OH:7])=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15](=[O:18])[NH:16]2)[CH2:20][NH:21][C:22]([CH3:33])([CH3:32])[CH2:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=1)[CH:30]=[O:31])([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:37])[CH3:36]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57989095(r)-Tert-butyl 5-(1-(tert-butyldimethylsilyloxy)-2-(1-(3-formylphenyl)-2-methylpropan-2-ylamino)ethyl)-2-oxo-1,2-dihydroquinolin-8-yl carbonate

Product 1

HCID 57989117(R)-3-(2-(2-(tert-Butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)-2-methylpropyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (R)-tert-butyl 5-(1-(tert-butyldimethylsilyloxy)-2-(1-(3-formylphenyl)-2-methylpropan-2-ylamino)ethyl)-2-oxo-1,2-dihydroquinolin-8-yl carbonate (Example 275, step g) (0.42 g) in methanol (15 mL) was treated with ammonia (35% aqueous) (2 mL). The reaction mixture was allowed to stand for 3 hours at 20° C. The solvent was removed under a stream of nitrogen and the residue was partitioned between ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate and the combined organics dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 0.34 g.

Workup

  1. customThe solvent was removed under a stream of nitrogen
  2. customthe residue was partitioned between ethyl acetate and brine
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organics dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-cf2204806024436c8ec325836871587e
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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