Bromine → 2-Benzyloxycarbonylmethoxyimino-4-bromo-3-oxobutyric acid

HRID 569363

Reaction equation

HRID 569363 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][O:12][N:13]=[C:14]([C:22](=[O:24])[CH3:23])[C:15]([O:17]C(C)(C)C)=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:25]Br>C(O)(=O)C>[CH2:1]([O:8][C:9]([CH2:11][O:12][N:13]=[C:14]([C:22](=[O:24])[CH2:23][Br:25])[C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 53811665Tert-butyl 2-benzyloxycarbonylmethoxyimino-3-oxobutyrate

Product 1

HCID 540321592-Benzyloxycarbonylmethoxyimino-4-bromo-3-oxobutyric acidYield 101.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of tert-butyl 2-benzyloxycarbonylmethoxyimino-3-oxobutyrate (32.3 g) in acetic acid (32 ml) was slowly added bromine (16 g) at 45° to 48° C. with stirring, and the stirring was continued at the same temperature for 30 minutes. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, followed by washing six times with a saturated aqueous sodium chloride. This solution was evaporated under reduced pressure to give 2-benzyloxycarbonylmethoxyimino-4-bromo-3-oxobutyric acid (35 g).

Workup

  1. customat 45° to 48° C.
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washby washing six times with a saturated aqueous sodium chloride
  5. customThis solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-eef14ec9e3334d10bd07feeb57874447
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Linked notes

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