Acetic Anhydride → L-Alanine, N-formyl-N-hydroxy-

HRID 434714Notes

Reaction equation

HRID 434714 reaction equation
S(O[CH:6]([CH3:14])[C:7]([O:9]C(C)(C)C)=[O:8])(C)(=O)=O.[Cl-].[OH:16][NH3+:17].C(N(CC)CC)C.C(O[C:29](=[O:31])C)(=O)C>CN1CCCC1=O.C(O)=O.C(OCC)C.O>[CH:29]([N:17]([OH:16])[C@H:6]([C:7]([OH:9])=[O:8])[CH3:14])=[O:31]

Participants

9

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 21645Hydroxylamine HClHCID 20491922t-Butyl 2-mesyloxypropionate

Product 1

HCID 6336523L-Alanine, N-formyl-N-hydroxy-

Reagents, catalysts & solvents 4

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

0.05 mole of this ester was then dissolved in 25 ml of N-methylpyrrolidone and 0.051 mole hydroxylammonium chloride and 0.1 mole of triethylamine were added. The mixture was stirred overnight at 50° C., after which time it was poured into water, diethyl ether was added, the organic layer was evaporated down and the resulting product was purified by chromatography over silica using diethyl ether and methylene chloride as eluants. (R) t-butyl 2-hydroxyaminopropionate, having an optical rotation in chloroform solution of +22.6°, was obtained. This material could then be reacted with formic acid and acetic anhydride as described in (B) above, to give the required product.

Workup

  1. additionwas added
  2. customthe organic layer was evaporated down
  3. customthe resulting product was purified by chromatography over silica
  4. customof +22.6°
  5. customwas obtained

Sources & evidence

ORD record
ord-8bf1cd35ae924952b504cdd6d1507569
Source dataset
uspto-grants-1983_08
Patent number
US04399149

Reaction notes

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