Ammonia → tert-Butyl (R)-2-(tert-butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate

HRID 471298Notes

Reaction equation

HRID 471298 reaction equation
C(OC([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[CH2:21][N:22]([C@H:30]([CH3:40])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]=[O:39])[CH:33]=2)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)=O)(C)(C)C.N>CO>[Si:42]([O:41][C@H:20]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:19])[NH:17]2)[CH2:21][N:22]([C@H:30]([CH3:40])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]=[O:39])[CH:33]=1)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:26])[CH3:27])([C:45]([CH3:46])([CH3:47])[CH3:48])([CH3:44])[CH3:43]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57989227tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate

Product 1

HCID 57989338tert-Butyl (R)-2-(tert-butyldimethylsilyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl (R)-2-(8-(tert-butoxycarbonyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilyloxy)ethyl((R)-1-(3-formylphenyl)propan-2-yl)carbamate (Example 276, step h) (0.521 g) was suspended in methanol (20 mL) and treated with ‘880’ aqueous ammonia (2.5 mL) to give a suspension that was stirred at room temperature for 3 hours. The mixture was concentrated by blowing with a stream of nitrogen, and the residue was partitioned between ethyl acetate, water and brine, and the phases separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo to afford the subtitled compound. Yield 0.476 g. Material used immediately in the next step.

Workup

  1. customto give a suspension that
  2. concentrationThe mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate, water and brine
  4. customthe phases separated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic phases were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51802a343408453aa512091ec98cd908
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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