Acetic Anhydride → HCID 13242805, compound

HRID 1016612Notes

Reaction equation

HRID 1016612 reaction equation
[CH2:1]([CH:8]([CH2:12][NH:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](OC(=O)C)(=[O:24])C>C(O)=O.ClCCl>[CH2:1]([CH:8]([CH2:12][N:13]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:22]=[O:24])[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 13242803HCID 13242803, compound

Product 1

HCID 13242805HCID 13242805, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(R,S)-benzyl-3-benzyloxyamino-propionic acid (7.8 g, 27.4 mmol) in formic acid (40 mL) was cooled in an ice-water bath and treated dropwise with acetic anhydride (15 mL). The reaction was allowed to warm to room temperature and stirred for 18 hours. The reaction mixture was diluted with dichloromethane (150 mL) and partitioned with water (100 mL). The organic layer was separated, washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure to yield 2-(R,S)-benzyl-3-(benzyloxy-formyl-amino)-propionic acid as a colourless oil (7.8 g, 91%). 1H-NMR; δ (CDCl3), 7.87-7.16 (10H, m), 4.924.66 (2H, m), 4.03-3.90 (2H, m), 3.17-2.93 (2H, m), 2.78-2.70 (1H, m).

Workup

  1. custompartitioned with water (100 mL)
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0db83764ced841e0818303521a93807a
Source dataset
uspto-grants-2002_11
Patent number
US06476067B1

Reaction notes

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