Water → HCID 131723611, compound

HRID 854400Notes

Reaction equation

HRID 854400 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][P:9]([CH2:19][NH:20][S:21]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)(=[O:23])=[O:22])(=[O:18])[O:10]C2C=CC=C(Cl)C=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].O>O1CCOCC1>[NH4+:20].[Cl:1][C:2]1[CH:3]=[C:4]([O:8][P:9]([CH2:19][NH:20][S:21]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)(=[O:23])=[O:22])(=[O:10])[O-:18])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22890939HCID 22890939, compound

Product 1

HCID 131723611HCID 131723611, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of diester (viii) (86 mg, 0.18 mmol) in dioxane (1.5 mL) was added 1 N sodium hydroxide solution (720 μL, 0.72 mmol) and water (4 mL). After 3 h, the solution was neutralized and concentrated. the residue was purified by flash chromatography (elution with chloroform:methanol:concentrated ammonium hydroxide; 8.2:2:0.25) to afford the title compound (28 mg, 40%) as a colorless solid: 1H NMR (400 MHz, D2O) δH 7.84 (d, J=5 Hz, 1H, Ar—H), 7.71 (d, J=3.5 Hz, Ar—H), 7.30 (t, J=8 Hz, 1H, Ar—H), 7.15-7.21 (m, 3H, Ar—H), 7.01-7.03 (m, 1H, Ar—H), 3.23 (d, J=14 Hz, 2H, NCH2P); 31P NMR: (164 MHz, D2O) δP 14.5.

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by flash chromatography (elution with chloroform:methanol:concentrated ammonium hydroxide; 8.2:2:0.25)

Sources & evidence

ORD record
ord-7209bed50591412cb413649d233369e4
Source dataset
uspto-grants-2007_08
Patent number
US07259172B2

Reaction notes

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