Dimethylformamide → Dibenzyl 4-chloro-3,3-dimethyl-4-oxobutyl phosphate

HRID 1968916Notes

Reaction equation

HRID 1968916 reaction equation
[CH2:1]([O:8][P:9]([O:19][CH2:20][CH2:21][C:22]([CH3:27])([CH3:26])[C:23](O)=[O:24])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.C(Cl)(=O)C([Cl:36])=O>ClCCl>[P:9]([O:19][CH2:20][CH2:21][C:22]([CH3:27])([CH3:26])[C:23]([Cl:36])=[O:24])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 672351544-{[Bis(benzyloxy)phosphoryl]oxy}-2,2-dimethylbutanoic acid

Product 1

HCID 86616512Dibenzyl 4-chloro-3,3-dimethyl-4-oxobutyl phosphate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the product from Example 11B (0.211 g, 0.538 mmol) in dichloromethane (1.35 mL) at 0° C. were added DMF (4 μL) and a solution of oxalyl chloride in dichloromethane (2M, 0.538 mL) and the mixture was stirred for 45 minutes at 0° C. The solvent was evaporated under reduced pressure and the residue was used without further purification.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was used without further purification

Sources & evidence

ORD record
ord-6f2b0ee761524fdeab48d2484955221f
Source dataset
uspto-grants-2013_04
Patent number
US08426388B2

Reaction notes

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