Ammonium Hydroxide → HCID 59868727, compound

HRID 383718Notes

Reaction equation

HRID 383718 reaction equation
[OH-].[NH4+].[CH2:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][N:4]1[C:13]1[N:18]=[C:17]([CH3:19])[C:16]([N:20](C(=O)CC(C)(C)C)[C:21](=[O:27])[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:15]([CH3:35])[N:14]=1>CO>[CH2:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][N:4]1[C:13]1[N:18]=[C:17]([CH3:19])[C:16]([NH:20][C:21](=[O:27])[CH2:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[C:15]([CH3:35])[N:14]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 59868754HCID 59868754, compound

Product 1

HCID 59868727HCID 59868727, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of ammonium hydroxide (30%, 1 ml) was added to a solution of 6f (0.031 g, 0.07 mmol) in methanol (1 ml) and stirred for 20 hours. The mixture was washed with brine and extracted with ethyl acetate. The organic layer was dried over MgSO4, concentrated and chromatographed to yield the title compound (0.019 g, 0.054 mmol, 77%). 1H NMR (CDCl3, 400 MHz) δ 1.11 (s, 9H), 2.23 (s, 2H), 2.30 (s, 6H), 2.91 (t, J=6.0 Hz, 2H), 4.04 (t, J=6.0 Hz, 2H), 4.89 (s, 2H), 6.68 (s, 1H), 7.17 (dd, J=7.8, 3.4 Hz, 4H).

Workup

  1. washThe mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed

Sources & evidence

ORD record
ord-6ec292ed31a146618fc52c0b6f98038f
Source dataset
uspto-grants-2013_02
Patent number
US08367684B2

Reaction notes

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