Potassium Carbonate → Tert-butyl (5-ethynyl-4-methylthiazol-2-yl)carbamate

HRID 1009033Notes

Reaction equation

HRID 1009033 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[S:9][C:10]([C:14]#[C:15][Si](C)(C)C)=[C:11]([CH3:13])[N:12]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[S:9][C:10]([C:14]#[CH:15])=[C:11]([CH3:13])[N:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86630950(4-Methyl-5-trimethylsilanylethynyl-thiazol-2-yl)-carbamic acid tert-butyl ester

Product 1

HCID 86630951Tert-butyl (5-ethynyl-4-methylthiazol-2-yl)carbamateYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the above prepared (4-methyl-5-trimethylsilanylethynyl-thiazol-2-yl)-carbamic acid tert-butyl ester (0.592 g, 1.907 mmol), dissolved in 10 mL of MeOH, was added K2CO3 (0.395 g, 1.5 eq.)) and the mixture was stirred for 2 h at ambient temperature. Pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with water and brine, drying over sodium sulfate, and evaporation to dryness, followed by flash chromatography (SiO2, hexane/ethyl acetate=4/1), produced 0.391 g of the title compound as light brown foam.

Workup

  1. additionPouring
  2. extractionice/NH4Cl, twofold extraction with ethyl acetate
  3. washwashing with water and brine
  4. dry with materialdrying over sodium sulfate, and evaporation to dryness

Sources & evidence

ORD record
ord-71cc0c9715ef459a899dd3a5333bd408
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

Loading…