Sodium Bicarbonate → 3-{(Isobutanoyloxyisobutoxy]carbonylamino}propyl(n-butyl)phosphinic Acid Sodium Salt

HRID 732342Notes

Reaction equation

HRID 732342 reaction equation
[C:1]([O:6][C@H:7]([O:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][P:18]([CH2:21][CH2:22][CH2:23][CH3:24])(=[O:20])[OH:19])=[O:13])[CH:8]([CH3:10])[CH3:9])(=[O:5])[CH:2]([CH3:4])[CH3:3].C([O-])(O)=O.[Na+:29]>O.C(#N)C>[Na+:29].[C:1]([O:6][CH:7]([O:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][P:18]([CH2:21][CH2:22][CH2:23][CH3:24])(=[O:19])[O-:20])=[O:13])[CH:8]([CH3:10])[CH3:9])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 866208323-{[(1R)-Isobutanoyloxyisobutoxy]carbonylamino}propyl(n-butyl)phosphinic Acid

Product 1

HCID 874593993-{(Isobutanoyloxyisobutoxy]carbonylamino}propyl(n-butyl)phosphinic Acid Sodium Salt

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 39 was dissolved in a mixture of water and acetonitrile, an aqueous solution of 1 eq. NaHCO3 was added, the mixture stirred for about 10 min, and lyophilized to afford the title compound (213). 1H-NMR (400 MHz, CDCl3): δ 6.55 (d, J=4.8 Hz, 1H), 3.10 (t, J=6.4 Hz, 2H), 2.53-2.56 (m, 1H), 1.97-2.00 (m, 1H), 1.79-1.83 (m, 2H), 1.70-1.74 (m, 2H), 1.53-1.58 (m, 2H), 1.37-1.43 (m, 2H), 1.15 (t, J=6.8 Hz, 6H), 0.90 (t, J=7.2 Hz, 9H).

Sources & evidence

ORD record
ord-d5fac6f631bd463d9e9522ee17748281
Source dataset
uspto-grants-2009_09
Patent number
US07585996B2

Reaction notes

Loading…