Diisopropylethylamine → 3-(8-Bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepine-2-yl)-4,4-dimethyloxazolidin-2-one

HRID 708107Notes

Reaction equation

HRID 708107 reaction equation
ClC(Cl)(O[C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.[Br:13][C:14]1[CH:15]=[CH:16][C:17]2[C:23]3[N:24]=[C:25]([NH:27][C:28](C)([CH3:31])[CH2:29]O)[S:26][C:22]=3[CH2:21][CH2:20][O:19][C:18]=2[CH:33]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Br:13][C:14]1[CH:15]=[CH:16][C:17]2[C:23]3[N:24]=[C:25]([N:27]4[C:28]([CH3:29])([CH3:31])[CH2:7][O:6][C:5]4=[O:11])[S:26][C:22]=3[CH2:21][CH2:20][O:19][C:18]=2[CH:33]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 582042622-(8-Bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepine-2-ylamino)-2-methylpropan-1-ol

Product 1

HCID 582038853-(8-Bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepine-2-yl)-4,4-dimethyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphosgene (148 mg, 0.500 mmol) was added to a mixture of 185 mg (0.500 mmol) of 2-(8-bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepine-2-ylamino)-2-methylpropan-1-ol and 0.522 ml (3.00 mmol) of diisopropylethylamine in 7.0 ml of methylene chloride. The reaction mixture was stirred for 3 hours and concentrated in vacuum. The residue was partitioned between ethyl acetate and 5% aqueous citric acid. The organic extracts were washed with water, brine, dried over magnesium sulfate and concentrated in vacuum. Yield 194 mg (98%). MS(ESI+): 396.3

Workup

  1. concentrationconcentrated in vacuum
  2. customThe residue was partitioned between ethyl acetate and 5% aqueous citric acid
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-76fffcf55c7c4f47a3813736ea462db8
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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