Lithium Hydroxide → 9-Bromo-4,5-dihydrobenzo[2,3]oxepino[4,5-D]thiazole-2-carboxylic acid

HRID 1848978Notes

Reaction equation

HRID 1848978 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]2[CH2:9][CH2:10][O:11][C:12]3[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:13]=3[C:14]=2[N:15]=1)=[O:5])C.[Li+].[OH-].C1COCC1>O>[Br:20][C:17]1[CH:18]=[CH:19][C:12]2[O:11][CH2:10][CH2:9][C:8]3[S:7][C:6]([C:4]([OH:5])=[O:3])=[N:15][C:14]=3[C:13]=2[CH:16]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67050521Ethyl 9-bromo-4,5-dihydrobenzo[2,3]oxepino[4,5-D]thiazole-2-carboxylate

Product 1

HCID 582039379-Bromo-4,5-dihydrobenzo[2,3]oxepino[4,5-D]thiazole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 9-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid ethyl ester (2.52 g, 7.11 mmol) and LiOH (1.53 g, 36.6 mmol) was added THF (6.5 mL) and water (6.5 mL) and allowed to stir at room temperature overnight. The reaction mixture was concentrated under reduced pressure to remove the THF. The reaction mixture was diluted with EtOAc and 1 N HCl and warmed in a water bath to solubilize the solid. The layers were separated and the organic extract was washed sequentially with water and brine. The combined organic extracts were dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure to give 9-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid. LC/MS (ESI+): m/z 327 (M+H)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove the THF
  3. additionThe reaction mixture was diluted with EtOAc and 1 N HCl
  4. temperaturewarmed in a water bath
  5. customThe layers were separated
  6. extractionthe organic extract
  7. washwas washed sequentially with water and brine
  8. dry with materialThe combined organic extracts were dried over MgSO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9410d20fa88a47688c532f20be8aea15
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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