Dichloromethane → di-tert-butyl (2R,3R)-2-(diethoxyphosphoryloxy)-3-hydroxysuccinate

HRID 1775772Notes

Reaction equation

HRID 1775772 reaction equation
[C:1]([CH:8]([CH:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[OH:11])[OH:9])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].ClCCl.C(N(CC)CC)C.[CH2:29]([O:31][P:32](Cl)(=[O:36])[O:33][CH2:34][CH3:35])[CH3:30]>O>[CH2:29]([O:31][P:32]([O:11][C@H:10]([C@@H:8]([OH:9])[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([O:33][CH2:34][CH3:35])=[O:36])[CH3:30]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 281630Di-tert-butyl tartrate

Product 1

HCID 131734750di-tert-butyl (2R,3R)-2-(diethoxyphosphoryloxy)-3-hydroxysuccinateYield 33.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(Step 1) To di-tert-butyl tartrate (182 mg, 0.692 mmol), dichloromethane (1.73 mL), triethylamine (0.145 mL, 1.04 mmol), and diethylchlorophosphoric acid (0.050 mL, 0.346 mmol) were added, and the resulting mixture was stirred at room temperature for 20 hours. To the reaction mixture, water was added, and the resulting mixture was extracted with chloroform. The organic layer was dried, over sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica, gel column chromatography (ethyl acetate/n-hexane=5/95 to 30/70), whereby di-tert-butyl (2R,3R)-2-(diethoxyphosphoryloxy)-3-hydroxysuccinate (46 mg, 33%) was obtained.

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried, over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica, gel column chromatography (ethyl acetate/n-hexane=5/95 to 30/70)

Sources & evidence

ORD record
ord-9de6878c1981443685be8b59191e80b1
Source dataset
uspto-grants-2016_02
Patent number
US09260459B2

Reaction notes

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