Chloromethyl Methyl Ether → HCID 54092582, compound

HRID 1978130Notes

Reaction equation

HRID 1978130 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][O:11][CH2:12]Cl.[OH:14][C@H:15]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1)[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>ClCCl.O>[CH3:10][O:11][CH2:12][O:14][C@H:15]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[CH:29][CH:28]=1)[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 54567442HCID 54567442, compound

Product 1

HCID 54092582HCID 54092582, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (1.15 ml) and chloromethyl methyl ether (0.5 ml) were added to a solution of benzyl (R)-2-hydroxyl-3-(4-morpholinophenyl)propionate (1.5 g) in dichloromethane (15 ml) under ice-cooling and the mixture was stirred at room temperature for 19 hours. This reaction mixture was diluted with water (40 ml) and extracted with ethyl acetate (20 ml×3). The organic layer was washed serially with 5% sodium hydrogencarbonate solution (20 ml), water (20 ml) and saturated aqueous solution of sodium chloride (20 ml) in the order mentioned and dehydrated over anhydrous sodium sulfate and the solvent was then distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography, elution being carried out with hexane-ethyl acetate (1:2, v/v). From the fraction containing the objective compound, the solvent was distilled off under reduced pressure to provide 1.73 g of benzyl (R)-2-methoxymethoxy-3-(4-morpholinophenyl)propionate.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (20 ml×3)
  3. washThe organic layer was washed serially with 5% sodium hydrogencarbonate solution (20 ml), water (20 ml) and saturated aqueous solution of sodium chloride (20 ml) in the order
  4. distillationthe solvent was then distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography, elution
  6. additionFrom the fraction containing the objective compound
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f5bb647b51854231aa71ca62cb416d82
Source dataset
uspto-grants-2001_05
Patent number
US06235875B1

Reaction notes

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