Water → DiiSopropyl ((1-(hydroxymethyl)cyclopropoxy)methyl)phosphonate

HRID 1714494Notes

Reaction equation

HRID 1714494 reaction equation
O.C(O)(C(F)(F)F)=O.[OH-].[Na+].[CH:11]([O:14][P:15]([CH2:21][O:22][C:23]1([CH2:26][O:27]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:25][CH2:24]1)(=[O:20])[O:16][CH:17]([CH3:19])[CH3:18])([CH3:13])[CH3:12]>CC(C)=O>[OH:27][CH2:26][C:23]1([O:22][CH2:21][P:15](=[O:20])([O:14][CH:11]([CH3:13])[CH3:12])[O:16][CH:17]([CH3:18])[CH3:19])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 11511792DiiSopropyl ((1-((trityloxy)methyl)cyclopropoxy)methyl)phosphonate4×

Product 1

HCID 11608665DiiSopropyl ((1-(hydroxymethyl)cyclopropoxy)methyl)phosphonate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound of formula (10) obtained in Example 3 (59.15 g, 116.3 mmol) was dissolved in acetone [59.2 ml, 1 ml/g with respect to the compound of formula (10)], H2O (5.9 ml, 327.8 mmol) and TFA (26.52 g, 232.6 mmol) were added, and the mixture was stirred at room temperature. After the portion of the compound of formula (10) was confirmed 7% or less by HPLC, 3N aqueous NaOH solution [75 ml, 2.6 ml/g with respect to the compound of formula (10)] was added thereto, and acetone was removed therefrom by distillation under reduced pressure. The solid produced during the reaction was filtered off, and the filtrate was extracted twice with methylene chloride [118.3 ml×2, 2 ml/g with respect to the compound of formula (10)]. Thus obtained organic layer was concentrated under reduced pressure to give the title compound (2) [31.71 g, Purity 98%, Yield with respect to the compound of formula (10) 102.4%].

Workup

  1. additionwere added
  2. additionwas added
  3. customacetone was removed
  4. distillationby distillation under reduced pressure
  5. customThe solid produced during the reaction
  6. filtrationwas filtered off
  7. extractionthe filtrate was extracted twice with methylene chloride [118.3 ml×2, 2 ml/g with respect to the compound of formula (10)]
  8. concentrationThus obtained organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2e2c89349ad344ed9d32292baae08ec1
Source dataset
uspto-grants-2010_09
Patent number
US07795463B2

Reaction notes

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