2,2-Dimethoxypropane → HCID 67470545, compound

HRID 407909Notes

Reaction equation

HRID 407909 reaction equation
[CH2:1]([O:8][C@H:9]([C@@H:13]([OH:17])[C:14]([OH:16])=[O:15])[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:20](OC)([CH3:22])[CH3:21].O.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>O>[CH2:1]([O:8][C@H:9]([C@@H:13]1[C:14](=[O:16])[O:15][C:20]([CH3:22])([CH3:21])[O:17]1)[C:10]([OH:12])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 13515957HCID 13515957, compound

Product 1

HCID 67470545HCID 67470545, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(2R,3R)-2-(Benzyloxy)-3-hydroxysuccinic acid (11.1 g, 46.2 mmol) was dissolved in 2,2-dimethoxypropane (46 mL, 374 mmol) and 4-methylbenzenesulfonic acid hydrate (0.0879 g, 0.462 mmol) was added and the reaction was stirred at ambient temperature for 4 hours. Water (30 mL) and NaHCO3 (0.0388 g, 0.462 mmol) were added and extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated to provide (R)-2-(benzyloxy)-2-((R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid. The crude product was taken on to next step without further purification.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2f779dc55318462dbb8c529c216063a8
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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