Ammonium Chloride → HCID 86656372, compound

HRID 1942550Notes

Reaction equation

HRID 1942550 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([N:14]([CH:44]([CH3:46])[CH3:45])[C:15]([C:17]2[C:18]([C:40]([F:43])([F:42])[F:41])=[CH:19][C:20]3[O:25][C:24]([CH3:31])(C(OCC)=O)[C:23](=[O:32])[N:22]([CH2:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[C:21]=3[CH:39]=2)=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Mg]Br.[Cl-].[NH4+]>O1CCCC1>[OH:5][C:1]([C:24]1([CH3:31])[C:23](=[O:32])[N:22]([CH2:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[C:21]2[CH:39]=[C:17]([C:15]([N:14]([CH:44]([CH3:45])[CH3:46])[C@@H:10]3[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9]3)=[O:16])[C:18]([C:40]([F:43])([F:41])[F:42])=[CH:19][C:20]=2[O:25]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 67333468HCID 67333468, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 86656372HCID 86656372, compoundYield 151.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 6-{[[(3R)-1-(tert-butoxycarbonyl)piperidin-3-yl](isopropyl)amino]-carbonyl}-4-(4-methoxybutyl)-2-methyl-3-oxo-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate (150 mg) in tetrahydrofuran (2 ml) was cooled with ice, and thereto was added dropwise methylmagnesium bromide (1M tetrahydrofuran solution, 1.2 ml), and the mixture was stirred at room temperature for 3 hours. To the reaction solution 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. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (111 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8071cadc03d54f9f8f93a48ea859cb88
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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