Hydrochloric Acid → {7-Bromo-4-[3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetic acid

HRID 1054179Notes

Reaction equation

HRID 1054179 reaction equation
[Li+].[OH-].[Br:3][C:4]1[CH:32]=[CH:31][C:7]2[N:8]([C:18]([C:20]3[CH:21]=[CH:22][C:23]4[O:28][CH2:27][C:26](=[O:29])[NH:25][C:24]=4[CH:30]=3)=[O:19])[CH:9]([CH2:12][C:13]([O:15]CC)=[O:14])[CH2:10][O:11][C:6]=2[CH:5]=1.CCOC(C)=O.Cl>O.C1COCC1>[Br:3][C:4]1[CH:32]=[CH:31][C:7]2[N:8]([C:18]([C:20]3[CH:21]=[CH:22][C:23]4[O:28][CH2:27][C:26](=[O:29])[NH:25][C:24]=4[CH:30]=3)=[O:19])[CH:9]([CH2:12][C:13]([OH:15])=[O:14])[CH2:10][O:11][C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 131736333Ethyl {7-bromo-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetate2×

Product 1

HCID 118599755{7-Bromo-4-[3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetic acidYield 108%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

LiOH (55.3 mg, 2.31 mmol) dissolved in water (3 mL) was added to a solution of ethyl {7-bromo-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetate (Intermediate 28, 366 mg, 0.77 mmol) in THF (6.0 mL). The mixture was stirred at rt for 1.5 h. EtOAc (40 mL) was added followed by 1 M HCl (3.1 mL, 3.1 mmol) and water (20 mL). The phases were separated and the organic layer was washed with brine (30 mL), dried over Na2SO4 and evaporated to give crude title compound (372 mg, 108%) as a solid.

Workup

  1. customThe phases were separated
  2. washthe organic layer was washed with brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-cd9d5e4df2d14a729317bf13df1c674f
Source dataset
uspto-grants-2016_07
Patent number
US09394291B2

Reaction notes

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