Dichloromethane → HCID 67926768, compound

HRID 981766Notes

Reaction equation

HRID 981766 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4]([CH2:6][C:7]([OH:9])=[O:8])[OH:5].C(OC(=NC(C)C)NC(C)C)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:28](Cl)Cl>CN(C=O)C>[CH3:28][O:8][C:7](=[O:9])[CH2:6][CH:4]([OH:5])[C:3]([O:2][CH2:1][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11128254o-Benzyl-n,n'-diisopropylisoureaHCID 121005551-Methyl malate

Product 1

HCID 67926768HCID 67926768, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Malic acid monomethyl ester (Example 2A) was dissolved in DMF and one equivalent of O-benzyl-N,N'-diisopropylisourea was added. The reaction mixture was stirred at room temperature for about 17 hours. Methylene chloride was added to the mixture and the suspension was filtered to remove the diisopropylurea. The filtrate was further diluted with methylene chloride and washed with water, 10% aqueous sodium carbonate, water, and with brine and was dried over magnesium sulfate. After filtration and evaporation the monobenzyl monomethyl ester was obtained as an oil.

Workup

  1. filtrationthe suspension was filtered
  2. customto remove the diisopropylurea
  3. additionThe filtrate was further diluted with methylene chloride
  4. washwashed with water, 10% aqueous sodium carbonate, water
  5. dry with materialwith brine and was dried over magnesium sulfate
  6. filtrationAfter filtration and evaporation the monobenzyl monomethyl ester
  7. customwas obtained as an oil

Sources & evidence

ORD record
ord-4386ffe2627e4225bdb58f6ef0a8da7e
Source dataset
uspto-grants-1991_02
Patent number
US04992544

Reaction notes

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