Lithium Hydroxide → 9-Bromo-5,6-dihydrobenzo[F]imidazo[1,2-D][1,4]oxazepine-2-carboxylic acid

HRID 1629568Notes

Reaction equation

[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]3[N:7]([CH:11]=[C:12]([C:14]([O:16]C)=[O:15])[N:13]=3)[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.[Li+].[OH-]>C1COCC1.O>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6]3[N:7]([CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=3)[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

methyl 9-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate (3.5 g, 10.8 mmol) and LiOH (0.52 g, 21.7 mmol) were dissolved in a mixture of THF:H2O (1:1, 150 mL). After the resulting mixture was stirred at 70° C. for 2 h, the water phase of the reaction mixture was separated, adjusted to pH 4.0 and extracted with EtOAc (100 mL×4). The organic phase was pooled and concentrated to give product (3.0 g, 90.5%). LCMS (ESI): m/z 310.6 (M+H+)

Workup

customthe water phase of the reaction mixture was separated
extractionextracted with EtOAc (100 mL×4)
concentrationconcentrated

Sources & evidence

ORD record: ord-4d1013db001c4c68839ba3af61e062dc
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785626B2

Reaction notes

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