Sodium hydride → [4-(4-tert-Butoxycarbonylmethoxy-3-methyl-phenyldisulfanyl)-2-methyl-phenoxy]-acetic acid tert-butyl ester

HRID 1242320Notes

Reaction equation

HRID 1242320 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([S:8][S:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([CH3:17])[CH:11]=2)[CH:5]=[CH:4][C:3]=1[OH:18].[C:19]([O:23][C:24](=[O:27])[CH2:25]Br)([CH3:22])([CH3:21])[CH3:20].[H-].[Na+]>CN(C=O)C.CCOCC>[C:19]([O:23][C:24](=[O:27])[CH2:25][O:16][C:13]1[CH:14]=[CH:15][C:10]([S:9][S:8][C:6]2[CH:5]=[CH:4][C:3]([O:18][CH2:25][C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:27])=[C:2]([CH3:1])[CH:7]=2)=[CH:11][C:12]=1[CH3:17])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 115364374,4'-Disulfanediylbis(2-methylphenol)

Product 1

HCID 86597804[4-(4-tert-Butoxycarbonylmethoxy-3-methyl-phenyldisulfanyl)-2-methyl-phenoxy]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To an ice cooled solution of 4.75 g (17.06 mmol) 4,4′-dithio-bis-(2-methyl-phenol) and 5.55 ml (37.6 mmol) bromo-acetic acid tert-butyl ester in 50 ml DMF was added 204 mg (85.3 mmol) sodium hydride (55% in oil). The reaction mixture was stirred over night at RT and then it was taken up in ether, washed with 1N HCl and water. The crude product was purified by chromatography over silica gel with AcOEt/heptane 1:4 providing 3.4 g pure [4-(4-tert-butoxycarbonylmethoxy-3-methyl-phenyldisulfanyl)-2-methyl-phenoxy]-acetic acid tert-butyl ester.

Workup

  1. washwashed with 1N HCl and water
  2. customThe crude product was purified by chromatography over silica gel with AcOEt/heptane 1:4 providing 3.4 g pure [4-(4-tert-butoxycarbonylmethoxy-3-methyl-phenyldisulfanyl)-2-methyl-phenoxy]-acetic acid tert-butyl ester

Sources & evidence

ORD record
ord-c7ccfa1e2a914632a5f87bc06964ca43
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

Loading…