Реакция #1519076

Уравнение реакции

alanine

tris(hydroxymethyl)phosphine

174.09

→

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

Выход 95.0%

Растворители

water

water

Условия реакции

Обработка

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

Методика

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): δ1.37 (d, 9H, —CH(CH3), 3.47 (d, 6H, P—(CH2)), 3.65 (q, 3H, —CH(CH3); 13C NMR (D2O, 75 MHz): δ14.84 (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).

Источник