L-Alanine → Propanoic acid, 2-(acetyloxy)-, (2R)-

HRID 1487178Notes

Reaction equation

HRID 1487178 reaction equation
N[C@@H:2]([CH3:6])[C:3]([OH:5])=[O:4].N([O-])=O.[Na+]>C(O)(=O)C>[C:3]([O:5][C@H:2]([CH3:6])[C:3]([OH:5])=[O:4])(=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 5950L-AlanineHCID 23668193Sodium Nitrite

Product 1

HCID 5325906Propanoic acid, 2-(acetyloxy)-, (2R)-Yield 67.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of (S)-2-aminopropanoic acid (60 g, 0.67 mol) in acetic acid (400 ml) was added NaNO2 (93 g, 1.34 mol) several portions at 0° C. After addition, the mixture was stirred at room temperature for 4 hours. After removed the acetic acid, water added and then extracted with ether. The organic phase was collected, dried, concentrated to afford (R)-2-acetoxypropanoic acid (30 g, 35%). 1H NMR (400 MHz, CDCl3) δ ppm, 11.70 (s, 2H), 5.02-5.07 (q, 1H), 2.07 (s, 3H), 1.46-1.52 (d, 3H).

Workup

  1. additionAfter addition
  2. customAfter removed the acetic acid, water
  3. additionadded
  4. extractionextracted with ether
  5. customThe organic phase was collected
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aa389296af8b4c4f87b5b09d7ba734c6
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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