Reacción #1894514

Ecuación de reacción

174.09

tris(hydroxymethyl)phosphine

alanine

→

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

Rendimiento 95.0%

Disolventes

water

water

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente