Hydrochloric Acid → (((4-Morpholinyl)carbonyl)oxy)-4-methylpentanoic Acid Methyl Ester

HRID 847611Notes

Reaction equation

HRID 847611 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4]([OH:9])[CH2:5][CH:6]([CH3:8])[CH3:7].[C:11](Cl)(Cl)=[O:12].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.Cl>C1(C)C=CC=CC=1.CN(C)C=O.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:10])[CH:4]([O:9][C:11]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:12])[CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 8083MorpholineHCID 62908Methyl 2-hydroxy-4-methylpentanoate

Product 1

HCID 53850443(((4-Morpholinyl)carbonyl)oxy)-4-methylpentanoic Acid Methyl Ester

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To 2-hydroxy-4-methylpentanoic acid methyl ester was added 150 ml of 12.5% phosgene in toluene and 25 drops of dimethylformamide. After stirring for 16 h at room temperature, the solvent was evaporated and the residue chased several times with benzene. The resulting product was dissolved in methylene chloride (50 ml), cooled to 0° C. and treated by dropwise addition with 3.86 g (0.044 mol) of morpholine. The reaction mixture was stirred for 2 h at 0°-5° C. and then distributed between 0.5N HCl and methylene chloride. The organic phase was washed with aqueous NaHCO3 and brine and evaporated to a residue. Flash chromatography on silica gel gave the desired compound.

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe resulting product was dissolved in methylene chloride (50 ml)
  3. temperaturecooled to 0° C.
  4. stirringThe reaction mixture was stirred for 2 h at 0°-5° C.
  5. washThe organic phase was washed with aqueous NaHCO3 and brine
  6. customevaporated to a residue

Sources & evidence

ORD record
ord-1dac4b6f9e214175a84ea11e844629ac
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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