tert-Butanol → tert-Butyl (4-{[methoxy(methyl)amino]methyl}-1,3-thiazol-2-yl)carbamate

HRID 1685049Notes

Reaction equation

HRID 1685049 reaction equation
[CH3:1][O:2][N:3]([CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12](N2C=CN=C2)=[O:13])[S:9][CH:10]=1)[CH3:4].[C:19]([OH:23])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:12]([NH:11][C:8]1[S:9][CH:10]=[C:6]([CH2:5][N:3]([O:2][CH3:1])[CH3:4])[N:7]=1)=[O:13])([CH3:22])([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 6386tert-ButanolHCID 43819141HCID 43819141, compound

Product 1

HCID 43819142tert-Butyl (4-{[methoxy(methyl)amino]methyl}-1,3-thiazol-2-yl)carbamateYield 90%

Procedure

A mixture of Intermediate 28: 2-(N-imidazocarbonylamino)-4-(N-methoxy-N-methyl-aminomethyl)thiazole (23.3 g, 87.2 mmol) and anhydrous tert-butanol (140 mL) was stirred under an inert atmosphere and heated to 80 C. After 20 minutes, a clear solution was obtained. tert-Butanol was evaporated at reduced pressure and the oily residue was dissolved in hexane (200 mL) and washed with water (2×100 mL). The organic layer was dried over sodium sulfate, filtered and evaporated to afford the title compound as a colorless oil which crystallized on standing (21.4 g, 90% yield).

Workup

  1. temperatureheated to 80 C
  2. customa clear solution was obtained
  3. customtert-Butanol was evaporated at reduced pressure
  4. dissolutionthe oily residue was dissolved in hexane (200 mL)
  5. washwashed with water (2×100 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ca04deda325445e69bd38980b0099b36
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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