Methyl Benzoate → HCID 21192984, compound

HRID 1068235Notes

Reaction equation

HRID 1068235 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:18][CH:17]=[N:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[C:24](OC)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[S:18][C:17]([C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7150Methyl BenzoateHCID 21193145HCID 21193145, compoundHCID 178418339Butyllithium

Product 1

HCID 21192984HCID 21192984, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 30 mg of 1-t-butyloxycarbonyl-4-(thiazol-5-yl)piperidine (prepared by method of example 291) in 3 ml THF at −78° C. was added 0.123 mmol of n-BuLi. The reaction was stirred for 20 min, then 18 mg of methyl benzoate was added. The reaction was stirred for 1 hr at −78° C. The solvent was evaporated under reduced pressure. The residue was dissolved in 1:1 MeOH:Et2O then purified by prep TLC with 1:1 hexane:EtOAc to give 11 mg of the title compound.

Workup

  1. stirringThe reaction was stirred for 1 hr at −78° C
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in 1:1 MeOH
  4. customEt2O then purified by prep TLC with 1:1 hexane

Sources & evidence

ORD record
ord-143c9be883e049bb9be3c7487cf206fa
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

Loading…