tert-Butyl bromoacetate → HCID 86758101, compound

HRID 431449

Reaction equation

HRID 431449 reaction equation
[C:1]([N:5]([OH:10])[CH2:6][C:7]([OH:9])=[O:8])([CH3:4])(C)C.C(=N/O)/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14]C=1.BrCC(O[C:25]([CH3:28])([CH3:27])[CH3:26])=O.[Na]>CC(O)C.O>[C:25]([CH:6]([C:7]([OH:9])=[O:8])[N+:5]([O-:10])=[CH:1][C:4]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:12]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 4

HCID 79177tert-Butyl bromoacetateHCID 5324470Syn-benzaldehyde oximeHCID 5360545SodiumHCID 53867073HCID 53867073, compound

Product 1

HCID 86758101HCID 86758101, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

t-Butyl N-Hydroxyglycine. Z-Benzaldoxime (5.64 g, 46.61 mmol) and t-butyl bromoacetate (7.58 mL, 10 g, 51.27 mmol) were added successively to a solution of sodium (1.07 g, 0.047 g-atom) in 2-propanol (120 mL). The suspension was stirred for 2 h and then poured into water (100 mL). Extraction with dichloromethane, followed by drying over anhydrous magnesium sulfate and concentration gave a residue which was chromatographed on silica gel. Elution with 60% ethyl acetate-hexanes gave t-butyl N-benzylideneglycine N-oxide.

Workup

  1. extractionExtraction with dichloromethane
  2. dry with materialby drying over anhydrous magnesium sulfate and concentration
  3. customgave a residue which
  4. customwas chromatographed on silica gel
  5. washElution with 60% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-a0116aa3708c45c29aef669b762b748d
Source dataset
uspto-grants-2003_12
Patent number
US06660734B1

Linked notes

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