Réaction #1894514

Équation de réaction

174.09

tris(hydroxymethyl)phosphine

alanine

→

2-[({Bis-[(1-carboxy-ethylamino)-methyl]-phosphanyl}-methyl)-amino]-propionic acid

Rendement 95.0%

Solvants

water

water

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was removed in vacuo
2. 2
   Autreto obtain a solid
3. 3
   LavageThe residue was washed in methanol (3×15 mL)
4. 4
   Autredried in vacuo
5. 5
   Autreto yield the analytically pure compound (THPAL) in 95% yield (2.58 g) as a white solid

Mode opératoire

As shown in Scheme II, alanine (2.15 g, 24.19 mmol) in 25 mL of distilled water was added to tris(hydroxymethyl)phosphine (1.00 g, 8.06 mmol) in water (15 mL) at 25° C. The reaction was stirred under dry nitrogen for one hour. The solvent was removed in vacuo to obtain a solid. The residue was washed in methanol (3×15 mL) and dried in vacuo to yield the analytically pure compound (THPAL) in 95% yield (2.58 g) as a white solid; ESI/MS calcd for C12H24N3O6P [M+H]+ 337.31, found 338.20; Anal. (calcd) for C12H24N3O6P: C, 42.73, H, 7.17. N 12.46. Found: C, 43.21, H, 7.54, N, 11.76; 1H NMR (D2O, 300 MHz): δ 1.37 (d, 9H, —CH(CH3), 3.47 (d, 6H, P—(CH2)), 3.65 (q, 3H, —CH(CH3); 13C NMR (D2O, 75 MHz): δ 14.84 (s, —CH(CH3), 42.65 (d, P—CH2, 1JP—C=12.83 Hz), 59.36 (d, CH(CH3),3JP—C=5.30 Hz), 174.09 (s, —COOH); 31P{1H} NMR (D2O, 121.5 MHz): −39.50 (s).

Source