Ammonia → HCID 57939028, compound

HRID 1436326Notes

Reaction equation

HRID 1436326 reaction equation
[C:1]([O:5][C:6](=[O:36])[N:7]([CH2:13][C:14]1[CH:19]=[C:18]([F:20])[C:17]([O:21][C:22]2[CH:34]=[CH:33][C:25]3[C:26](=O)[O:27]C(C)(C)[O:29][C:24]=3[CH:23]=2)=[C:16]([F:35])[CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[NH3:37]>C(O)(C)C>[C:1]([O:5][C:6](=[O:36])[N:7]([CH2:13][C:14]1[CH:19]=[C:18]([F:20])[C:17]([O:21][C:22]2[CH:34]=[CH:33][C:25]([C:26](=[O:27])[NH2:37])=[C:24]([OH:29])[CH:23]=2)=[C:16]([F:35])[CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 57939029HCID 57939029, compound

Product 1

HCID 57939028HCID 57939028, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

[4-(2,2-Dimethyl-4-oxo-4H-benzo[1,3]dioxin-7-yloxy)-3,5-difluoro-benzyl]-(3-methyl-butyl)-carbamic acid tert-butyl ester (I-1d-3: 1.0 g) was dissolved in 2.0 mL of a 2 M solution of ammonia in isopropanol. The resulting solution was then treated with 1.5 mL of a saturated aqueous ammonia solution and the resulting mixture heated at 80° C. After 8 hours, the reaction mixture was cooled to ambient temperature and concentrated with a rotary evaporator. The residue was diluted with ethyl acetate and the organic solution was washed twice with water, once with brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel eluting with 50% ethyl acetate in heptane to afford the title compound (I-1e-3).

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated with a rotary evaporator
  3. additionThe residue was diluted with ethyl acetate
  4. washthe organic solution was washed twice with water, once with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel eluting with 50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-eaef30d9c7e846fa80473af64450225e
Source dataset
uspto-grants-2009_11
Patent number
US07618996B2

Reaction notes

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