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

HRID 1154187Notes

Reaction equation

HRID 1154187 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-55613ad30b4045b3b46f6d2b3290a937
Source dataset
uspto-grants-1984_12
Patent number
US04487927

Reaction notes

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