Sodium Methoxide → HCID 70273828, compound

HRID 1420535Notes

Reaction equation

HRID 1420535 reaction equation
[F:1][CH:2]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:3][CH2:4][CH2:5][CH:6]([N:10]1[CH:13]([S:14][CH3:15])[C:12]([CH2:18][CH3:19])([CH2:16][CH3:17])[C:11]1=[O:20])[C:7]([O-])=[O:8].C(C1(CC)C(SC)[N:33](CC(OC)=O)C1=O)C.FC1C=CC(CCCCCCO)=CC=1.C[O-].[Na+]>C1C=CC=CC=1>[F:1][CH:2]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:3][CH2:4][CH2:5][CH:6]([N:10]1[CH:13]([S:14][CH3:15])[C:12]([CH2:18][CH3:19])([CH2:16][CH3:17])[C:11]1=[O:20])[C:7]([NH2:33])=[O:8]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 14739744HCID 14739744, compoundHCID 86755434HCID 86755434, compound

Product 1

HCID 70273828HCID 70273828, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Fluorophenylhexyl(3,3-diethyl-4-methylthio-2-oxoazetidin-1-yl)acetate-Methyl (3,3-diethyl-4-methylthio-2-oxo-azetidin-1-yl)acetate (0.8 g, 3.2 mmol) was dissolved in benzene with 4-fluorophenylhexylalcohol (1.3 g, 6.5 mmol) and sodium methoxide (SOmg ,0.9 mmol) and the mixture refuxed for 2 h. The reaction mixture was evaporated and diluted with EtOAc, the solution washed with water, separated, dried (K2CO3) and flash chromatographed (hexane/ethyl acetate 9:1) to give 4-fluorophenylhexyl(3,3-diethyl-4-methylthio-2-oxoazetidin-1-yl)acetamide 0.17 g, 14% as an oil.

Workup

  1. customThe reaction mixture was evaporated
  2. additiondiluted with EtOAc
  3. washthe solution washed with water
  4. customseparated
  5. dry with materialdried (K2CO3) and flash
  6. customchromatographed (hexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-ee21674b30a24065b1d6c41e22877861
Source dataset
uspto-grants-2000_06
Patent number
US06071899

Reaction notes

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