tert-Butyl methyl ether → HCID 88151757, compound

HRID 2298722Notes

Reaction equation

HRID 2298722 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][CH:5]=[N:4][C:3]1=[S:8].[Br:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:41])[CH2:24][CH2:25][C:26]2[CH:31]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:29]([OH:36])=[C:28]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:27]=2)=[CH:18][CH:17]=1)(=[O:15])=[O:14].C(OC)(C)(C)C>C(O)CC.C(OCC)(=O)C>[Br-:9].[C:32]([C:30]1[CH:31]=[C:26]([CH2:25][CH2:24][C:23]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([S:13]([NH:12][CH2:11][CH2:10][S:8][C:3]3[N:4]=[CH:5][CH:6]=[CH:7][N+:2]=3[CH3:1])(=[O:14])=[O:15])=[CH:17][CH:18]=2)=[O:41])[CH:27]=[C:28]([C:37]([CH3:39])([CH3:40])[CH3:38])[C:29]=1[OH:36])([CH3:33])([CH3:34])[CH3:35]

Participants

6

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 15607797HCID 15607797, compoundHCID 18339255HCID 18339255, compound

Product 1

HCID 88151757HCID 88151757, compound

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 1-methyl-1H-pyrimidine-2-thione (2.76 g, 0.0219 mol) and N-[4-(2-bromo-ethylsulfamoyl)-phenyl]-3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propionamide (9.98 g, 0.0185 mol) in 1-propanol (25 ml) was heated at reflux for 2.5 hours. The mixture was spin-evaporated in vacuo to give a solid residue. The residue was dissolved in ethyl acetate (200 g) and mixed with tert.-butyl-methyl ether (20 g) to give two liquid phases. The lower phase was concentrated in vacuo to give2-(2-{4-[3-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-propionylamino]-benzenesulfonylamino} -ethylsulfanyl)-1-methyl-pyrimidin-1-ium bromide.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. customThe mixture was spin-evaporated in vacuo
  4. customto give a solid residue
  5. customto give two liquid phases
  6. concentrationThe lower phase was concentrated in vacuo to give2-(2-{4-[3-(3,5-Di-tert-butyl-4-hydroxy-phenyl)-propionylamino]-benzenesulfonylamino} -ethylsulfanyl)-1-methyl-pyrimidin-1-ium bromide

Sources & evidence

ORD record
ord-b1890120990c4b46967a0179827337cd
Source dataset
uspto-grants-2002_12
Patent number
US06495125B2

Reaction notes

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