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

HRID 905413Notes

Reaction equation

HRID 905413 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. The 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. customThe solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-70bcbc49bea54e8b98055e4c66585fca
Source dataset
uspto-grants-1983_12
Patent number
US04423213

Reaction notes

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