Formic Acid → N-formyl-2-(benzyloxyaminomethyl)-4-methylpentanoic acid

HRID 982570Notes

Reaction equation

HRID 982570 reaction equation
[CH2:1]([O:8][NH:9][CH2:10][CH:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19](O)=[O:20]>C(OC(=O)C)(=O)C>[CH:19]([N:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:10][CH:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:12]([OH:14])=[O:13])=[O:20]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 193675172-(Benzyloxyaminomethyl)-4-methylpentanoic acid

Product 1

HCID 19367512N-formyl-2-(benzyloxyaminomethyl)-4-methylpentanoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

1.0 g of N-benzyloxy 2(RS)-isobutyl-3-amino-propionic acid in 10 ml of formic acid and 1 ml of acetic anhydride was stirred at room temperature for 2 hours and then evaporated. The residue was taken up in ethyl acetate, washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated to yield 1.2 g (100%) of N-formyl-N-benzyloxy 2(RS)-isobutyl-3-aminopropionic acid as a gum. Rf (toluene/acetic acid 4:1) 0.39.

Workup

  1. customevaporated
  2. washwashed with water and saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-c8e1c73d53384c25b9e7cbad90379926
Source dataset
uspto-grants-1991_02
Patent number
US04996358

Reaction notes

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