Isopropylamine → 2-Methylpropanoic acid (carboxymethylphosphonomethyl carbamoyloxy)-methyl ester-isopropylamine salt

HRID 843095Notes

Reaction equation

HRID 843095 reaction equation
[C:1]([CH2:4][O:5][P:6]([CH2:9][NH:10][C:11]([O:13][CH2:14][O:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])=[O:12])([OH:8])=[O:7])([OH:3])=[O:2].[CH:21]([NH2:24])([CH3:23])[CH3:22]>CC(C)=O>[CH:21]([NH2:24])([CH3:23])[CH3:22].[C:1]([CH2:4][O:5][P:6]([CH2:9][NH:10][C:11]([O:13][CH2:14][O:15][C:16](=[O:20])[CH:17]([CH3:18])[CH3:19])=[O:12])([OH:8])=[O:7])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 867579662-Methylpropanoic acid (carboxymethylphosphonomethylcarbamoyloxy)-methyl ester

Product 1

HCID 867579682-Methylpropanoic acid (carboxymethylphosphonomethyl carbamoyloxy)-methyl ester-isopropylamine saltYield 90.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred ice cold solution of 2-methylpropanoic acid (carboxymethylphosphonomethylcarbamoyloxy)-methyl ester (14.1 g, 43.8 mmol) in 80 mL of acetone was added isopropylamine (3.71 mL, 43.8 mmol). After 15 min of stirring the solvent was removed was removed under vacuum. The solid was washed with diethyl ether and subsequently dried under vacuum to afford 14.8 g of a tannish solid. 1H-NMR (300 MHz, D2O) δ (ppm): 1.01 (dd, 6H), 1.16 (d, 6H), 2.51 (m, 1H), 3.35 (m, 1H), 3.47 (d, 2H), 4.09 (d, 2H), 5.63 (d, 2H).

Workup

  1. customwas removed
  2. customwas removed under vacuum
  3. washThe solid was washed with diethyl ether
  4. customsubsequently dried under vacuum

Sources & evidence

ORD record
ord-e55d0862b0784cba84138ed9f8ca2ffb
Source dataset
uspto-grants-2002_04
Patent number
US06376548B1

Reaction notes

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