Ammonia → HCID 57010612, compound

HRID 2255471Notes

Reaction equation

HRID 2255471 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][NH:11][CH2:12][C:13]1[C:16](=[O:17])[C:15](=[O:18])[C:14]=1OCC)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[NH3:22]>>[CH2:1]([O:3][P:4]([CH2:9][CH2:10][NH:11][CH2:12][C:13]1[C:16](=[O:17])[C:15](=[O:18])[C:14]=1[NH2:22])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 57169422HCID 57169422, compound

Product 1

HCID 57010612HCID 57010612, compoundYield 77%

Procedure

An ethanolic solution (40 mL) of [2-[(2-ethoxy-3,4-dioxo-1-cyclobuten-1-yl)methylamino]ethyl]phosphonic acid diethyl ester (3.00 g, 9.40 mmol) was combined with ethanolic ammonia solution (70 mL) and left for 18 hours. After concentrating in vacuo, the solid was recrystallized twice from methanol in ethyl acetate (final volume=50 mL) to yield [2-[(2-amino-3,4-dioxo-1-cyclobuten-1-yl)methylamino]ethyl]phosphonic acid diethyl ester as a solid (2.10 g, 77%, mp 130°-132° C.); IR (KBr, cm-1): 3320, 3160, 1800, 1670, 1650, 1640; MS (+FAB): 291 (MH+, 100), 196 (22), 109 (20); 1H NMR (DMSO, 400 MHz): δ 7.61 (br s NH2), 4.02-3.94 (m, 4H), 3.74 (br s, 2H), 3.13 (br s, 3H), 2.13 (d of t, J= 18 and 7.5 Hz, 2H), 1.22 (t,J=7 Hz, 6H).

Workup

  1. concentrationAfter concentrating in vacuo
  2. customthe solid was recrystallized twice from methanol in ethyl acetate (final volume=50 mL)

Sources & evidence

ORD record
ord-43f1a1f71e7747889aa2d0b42ea44dcf
Source dataset
uspto-grants-1993_08
Patent number
US05240946

Reaction notes

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