Reaktion #1894514

Reaktionsgleichung

174.09

tris(hydroxymethyl)phosphine

alanine

→

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

Ausbeute 95.0%

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

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