HCID 73052642, compound → HCID 69098014, compound

HRID 1503081Notes

Reaction equation

HRID 1503081 reaction equation
CON(C)[C:4]([CH2:6][C:7]1([CH2:10][C:11]([OH:13])=[O:12])[CH2:9][CH2:8]1)=[O:5].[CH3:15][Li]>C1COCC1>[O:5]=[C:4]([CH3:15])[CH2:6][C:7]1([CH2:10][C:11]([OH:13])=[O:12])[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 73052642HCID 73052642, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 69098014HCID 69098014, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.6 g crude {1-[(methoxy-methyl-carbamoyl)-methyl]-cyclopropyl}-acetic acid (18 mmole) in 54 ml of THF are added 24.5 ml of methyllithium (1.6 M solution in diethyl ether, 39.2 mmole, 2.2 eq) at <−75° C. Stirring is continued for 2 hours, then the mixture is quenched by addition of 2 ml of methanol and warmed to room temperature. 54 ml of water are added and the phases are separated. The aqueous product phase is washed with 27 ml of methyl tert-butyl ether, acidified to pH 2.5 by addition of conc. HCl and extracted three times with 27 ml ethyl acetate each. The combined organic phases are concentrated to dryness and the residue is directly used in the next step (esterification to [1-(2-oxo-propyl)-cyclopropyl]-acetic acid methyl ester).

Workup

  1. customthe mixture is quenched by addition of 2 ml of methanol
  2. addition54 ml of water are added
  3. customthe phases are separated
  4. washThe aqueous product phase is washed with 27 ml of methyl tert-butyl ether
  5. additionacidified to pH 2.5 by addition of conc. HCl
  6. extractionextracted three times with 27 ml ethyl acetate each
  7. concentrationThe combined organic phases are concentrated to dryness

Sources & evidence

ORD record
ord-27fe9cdf95914b138e9851b3437845c4
Source dataset
uspto-grants-2015_12
Patent number
US09212120B2

Reaction notes

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