Ammonium Chloride → HCID 86656370, compound

HRID 1942549Notes

Reaction equation

HRID 1942549 reaction equation
[CH:1]([N:4]([C:18]([C:20]1[C:21]([C:44]([F:47])([F:46])[F:45])=[CH:22][C:23]2[O:28][C:27]([CH3:35])([CH2:29][O:30][CH2:31][CH:32]3[CH2:34][O:33]3)[C:26](=[O:36])[N:25]([CH2:37][CH2:38][CH2:39][CH2:40][O:41][CH3:42])[C:24]=2[CH:43]=1)=[O:19])[C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)([CH3:3])[CH3:2].[O-:48][CH2:49][CH3:50].[Na+].[Cl-].[NH4+]>O1CCCC1>[CH2:49]([O:48][CH2:34][CH:32]([OH:33])[CH2:31][O:30][CH2:29][C:27]1([CH3:35])[C:26](=[O:36])[N:25]([CH2:37][CH2:38][CH2:39][CH2:40][O:41][CH3:42])[C:24]2[CH:43]=[C:20]([C:18]([N:4]([CH:1]([CH3:2])[CH3:3])[C@@H:5]3[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:6]3)=[O:19])[C:21]([C:44]([F:47])([F:45])[F:46])=[CH:22][C:23]=2[O:28]1)[CH3:50]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2723922Sodium ethoxideHCID 86656371HCID 86656371, compound

Product 1

HCID 86656370HCID 86656370, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl (3R)-3-(isopropyl{[4-(4-methoxybutyl)-2-methyl-2-[(oxiran-2-ylmethoxy)methyl]-3-oxo-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}-amino)piperidine-1-carboxylate (113 mg) in tetrahydrofuran (1 ml) was added sodium ethoxide (0.1 ml, 20% ethanol solution), and the mixture was stirred at 50° C. for 2 hours. The reaction solution was cooled, and thereto was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. To the obtained residue was added acetic acid (1 ml), and the mixture was stirred at 50° C. for one hour. The solution was cooled to room temperature, and thereto was added ethyl acetate, and the organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (13 mg).

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. additionTo the obtained residue was added acetic acid (1 ml)
  8. stirringthe mixture was stirred at 50° C. for one hour
  9. temperatureThe solution was cooled to room temperature
  10. additionwas added ethyl acetate
  11. washthe organic layer was washed with water
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure
  15. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cbb79b1646f2475f91586afab7d88ffb
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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