反应 #1519076

反应方程式

alanine

tris(hydroxymethyl)phosphine

174.09

→

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

收率 95.0%

溶剂

water

water

反应条件

后处理

1. 1
   其他The solvent was removed in vacuo
2. 2
   其他to obtain a solid
3. 3
   洗涤The residue was washed in methanol (3×15 mL)
4. 4
   其他dried in vacuo
5. 5
   其他to yield the analytically pure compound (THPAL) in 95% yield (2.58 g) as a white solid

实验过程

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).

来源