Water → Tert-butyl (5-ethynylthiazol-2-yl)carbamate

HRID 1889180Notes

Reaction equation

HRID 1889180 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[S:9][C:10]([C:13]#[C:14][Si](C)(C)C)=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].O.C(OCC)(=O)C>CO>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[S:9][C:10]([C:13]#[CH:14])=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 45117882Tert-butyl (5-((trimethylsilyl)ethynyl)thiazol-2-yl)carbamate

Product 1

HCID 57737416Tert-butyl (5-ethynylthiazol-2-yl)carbamateYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (5-trimethylsilanylethynyl-thiazol-2-yl)-carbamic acid tert-butyl ester (1.67 g, 5.633 mmol) was dissolved in methanol (20 ml) was added K2CO3 (0.389 g, 2.816 mmol) and stirred at room temperature overnight. Then the reaction was heated at 50° C. for 2 hrs. Methanol was removed under reduced pressure. The residue obtained was partioned between water (50 ml) and ethyl acetate (50 ml). The layers were separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide (5-ethynyl-thiazol-2-yl)-carbamic acid tert-butyl ester (1.2 g).

Workup

  1. temperatureThen the reaction was heated at 50° C. for 2 hrs
  2. customMethanol was removed under reduced pressure
  3. customThe residue obtained
  4. customThe layers were separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2ece949582294b6d9827059fc272d45b
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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