Methanol → HCID 66862662, compound

HRID 252936Notes

Reaction equation

HRID 252936 reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].I[CH3:21].CO>CC#N.CCCCCC.CC(=O)OCC>[C:1]([N:8]1[CH2:9][CH:10]([N:12]([CH3:21])[C:13]2[S:14][CH:15]=[CH:16][N:17]=2)[CH2:11]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 79046843HCID 79046843, compound

Product 1

HCID 66862662HCID 66862662, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A suspension of 270 mg (1.05 mmol) of 1-Boc-3-(thiazol-2-ylamino)azetidine in MeCN (5 ml) was combined with 68 mg (1.2 mmol, 60% strength in mineral oil) of sodium hydride and stirred for 30 min at RT. 151 μl (1.73 mmol) of iodomethane were then added and stirring continued for a further 16 h at RT. After addition of MeOH (200 μl), evaporation under a vacuum was carried out. 166 mg (0.62 mmol, 59%) of 1-Boc-3-(methyl(thiazol-2-yl)amino)azetidine were obtained by CC (hexane/EA 3:2) with the residue.

Workup

  1. stirringstirring
  2. waitcontinued for a further 16 h at RT

Sources & evidence

ORD record
ord-2bb25d14ea6a4eb2823f2005d36584ff
Source dataset
uspto-grants-2011_01
Patent number
US07871999B2

Reaction notes

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