Sodium Azide → 3-Azido-L-alanine

HRID 1589920Notes

Reaction equation

HRID 1589920 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C@H:13]1[CH2:16][O:15][C:14]1=[O:17].[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C=O)C>[N:18]([CH2:16][C@@H:13]([C:14]([OH:15])=[O:17])[NH2:12])=[N+:19]=[N-:20]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 156005374-Methylbenzene-1-sulfonic acid--(3S)-3-aminooxetan-2-one (1/1)

Product 1

HCID 99640963-Azido-L-alanineYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (S)-3-amino-2-oxetanone p-toluenesulfonic acid salt (53.0 mg, 0.204 mmol) in DMF (1 mL) was added to NaN3 (14.6 mg, 0.225 mmol) in DMF (5 mL) and the mixture was stirred 3.5 h. The solvent was removed in vacuo at 25° C. The residue was dissolved in H2O (0.3 mL) and applied to a column of Bio-Rad Ion Retardation Resin Ag11 A8 (trademark) (15 g, 1×20 cm) and eluted with H2O (0.3 mL/min). Fractions containing amino acid were pooled and lyophilized to yield 25.6 mg (96%) of pure β-azido-L-alanine. For the optimum melting point this material was recrystallized by dissolving in a minimal volume of H2O at 40° C., adding MeOH (3 vol.) and acetone (until cloudy) and cooling to -20° C.: mp 174°-175° C. (dec); [α]D 25 +37.2 (± 0.5) (c 0.5, H2O); IR (K8r disk) 3420 (m, br), 3070 (s, br), 2113 (s), 1600 (vs, br), 1440 (s) cm-1 ; 1H NMR (300 MHz, d4 -MeOD)δ 3.63 (dd, 1H, 4.5, 12 Hz, CHHN3), 3.53 (dd, 1H, 7.2, 12 Hz, CHN3), 3.37 (dd, 1H, 4.5, 7.2 Hz, CH); 1H NMR (300 MHz, D2O)δ 3.93 (dd, 1H, 5.0, 17.5 Hz, CHHN3), 3.92 (m, 1H, CH), 3.84 (dd, 1H, 7.0, 17.5 Hz, CHHN3); EI-MS: 131.0570 (MH+, Calc. 131.0570 for C3H7N4O2), 88.0400 (MH+ -HN3), 85.0515 (M-CO2H), 74.0245 (Base peak, M-CH2N3); POSFAB-MS (glycerol) 131 (MH+); Rf 0.80 (System A; UV active; brown-purple with ninhydrin).

Workup

  1. customThe solvent was removed in vacuo at 25° C
  2. dissolutionThe residue was dissolved in H2O (0.3 mL)
  3. washeluted with H2O (0.3 mL/min)
  4. additionFractions containing amino acid

Sources & evidence

ORD record
ord-ed16f5330bc94bceaf42e8b9e6444a9c
Source dataset
uspto-grants-1993_04
Patent number
US05200526

Reaction notes

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