반응 #1519076

반응 방정식

alanine

tris(hydroxymethyl)phosphine

174.09

→

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

수율 95.0%

용매

water

water

반응 조건

후처리

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

실험 절차

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).

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