Reaction #1519076

Reaction equation

alanine

tris(hydroxymethyl)phosphine

174.09

→

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

Yield 95.0%

Solvents

water

water

Conditions

Workup

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

Procedure

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).

Source