Acetyl bromide → O-acetyl-N-benzyloxycarbonyl-L-threonine

HRID 2165232Notes

Reaction equation

HRID 2165232 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[C@@H:13]([CH3:15])[OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](Br)(=[O:21])[CH3:20]>C(O)(=O)C>[C:19]([O:14][C@H:13]([CH3:15])[C@@H:12]([C:16]([OH:18])=[O:17])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 10482Acetyl bromideHCID 88217N-((Benzyloxy)carbonyl)-L-threonine

Product 1

HCID 18640002O-acetyl-N-benzyloxycarbonyl-L-threonine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-threonine (5 g) in acetic acid (50 ml) was added acetyl bromide (1.75 ml) at room temperature. After stirring for an hour at room temperature, the reaction mixture was concentrated and the residue was diluted with ethyl acetate and washed successively with water (2 times) and brine. After drying over sodium sulfate, the ethyl acetate extract was filtered and concentrated to give O-acetyl-N-benzyloxycarbonyl-L-threonine (3.64 g).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed successively with water (2 times) and brine
  4. dry with materialAfter drying over sodium sulfate
  5. extractionthe ethyl acetate extract
  6. filtrationwas filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6db671a105ea4ab58a2b9cebaa021144
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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