L-Alanine → HCID 10286675, compound

HRID 1807332Notes

Reaction equation

HRID 1807332 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].O[CH2:8][P:9]([CH2:12]O)[CH2:10]O.[C:14]1(F)C(=O)NC(=O)[NH:16][C:15]=1[C:22]([OH:24])=[O:23]>O>[C:4]([CH:2]([NH:1][CH2:12][P:9]([CH2:8][NH:16][CH:15]([CH3:14])[C:22]([OH:24])=[O:23])[CH2:10][NH:1][CH:2]([C:4]([OH:6])=[O:5])[CH3:3])[CH3:3])([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 697115-Fluoroorotic acidHCID 76001Tris(Hydroxymethyl)Phosphine

Product 1

HCID 10286675HCID 10286675, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

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): 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).

Workup

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

Sources & evidence

ORD record
ord-dc3b9bef27d043f990137857a49028c4
Source dataset
uspto-grants-2013_01
Patent number
US08357349B2

Reaction notes

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