Acetic Anhydride → HCID 13242805, compound

HRID 2299173Notes

Reaction equation

HRID 2299173 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.C(Cl)Cl>[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 DCM (150 mL) and partitioned with water (100 mL). The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield 2-(R,S)-benzyl-3-(benzyloxy-formyl-amino)-propionic acid as a colorless oil (7.8 g, 91%). 1H-NMR; δ (CDCl3), 7.87-7.16 (10 H, m), 4.92-4.66 (2 H, m), 4.03-3.90 (2 H, m), 3.17-2.93 (2 H, m), 2.78-2.70 (1 H, m).

Workup

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

Sources & evidence

ORD record
ord-ed052c1d666f4bee94f9ebc5f27a1f2c
Source dataset
uspto-grants-2002_12
Patent number
US06495597B1

Reaction notes

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