Ammonia → HCID 57010612, compound

HRID 1681062Notes

Reaction equation

HRID 1681062 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-c2a1b3215592453aad14764b19631c6c
Source dataset
uspto-grants-1992_12
Patent number
US05168103

Reaction notes

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