Ammonia → HCID 57939025, compound

HRID 1436324Notes

Reaction equation

HRID 1436324 reaction equation
[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:33]=[CH:32][C:24]3[C:25](=O)[O:26]C(C)(C)[O:28][C:23]=3[CH:22]=2)=[C:16]([F:34])[CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[NH3:36]>C(O)(C)C>[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:33]=[CH:32][C:24]([C:25](=[O:26])[NH2:36])=[C:23]([OH:28])[CH:22]=2)=[C:16]([F:34])[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 57939032HCID 57939032, compound

Product 1

HCID 57939025HCID 57939025, 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-fluoro-benzyl]-(3-methyl-butyl)-carbamic acid tert-butyl ester (I-1d-1: 20 g) was dissolved in 35 mL of a 2 M solution of ammonia in isopropanol. The resulting solution was then treated with 50 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-1).

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-a3197183bdbf46d2a47055b14cfe24bd
Source dataset
uspto-grants-2009_11
Patent number
US07618996B2

Reaction notes

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