Diethyl Ether → HCID 10090158, compound

HRID 981286Notes

Reaction equation

HRID 981286 reaction equation
Br.C(O)(=O)C.C(OC([NH:16][C:17]1([C:20]2[C:21]([F:41])=[CH:22][C:23]3[C:34](=[O:35])[C:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:32][N:25]4[CH:26]([CH2:30][F:31])[CH2:27][O:28][C:29]=2[C:24]=34)[CH2:19][CH2:18]1)=O)C1C=CC=CC=1.C(OCC)C>O>[NH2:16][C:17]1([C:20]2[C:21]([F:41])=[CH:22][C:23]3[C:34](=[O:35])[C:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:32][N:25]4[CH:26]([CH2:30][F:31])[CH2:27][O:28][C:29]=2[C:24]=34)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11755634HCID 11755634, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 10090158HCID 10090158, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 ml of a 30% hydrogen bromide-acetic acid solution was added to 52 mg of ethyl 10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro-3-fluoromethyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6carboxylate. The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. To the residue obtained were added 10 ml of diethyl ether and 20 ml of water in this order. The aqueous layer was separated and 20 ml of ethyl acetate was added thereto. The resulting mixture was adjusted to pH 8.5 with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 35 mg (yield: 90.8%) of ethyl 10-(1-aminocyclopropyl)-9-fluoro-3-fluoromethyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customTo the residue obtained
  3. customThe aqueous layer was separated
  4. addition20 ml of ethyl acetate was added
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-224698f309b2466bbe0ed853a9037591
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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