tert-Butyl (4-(methoxy(methyl)carbamoyl)thiazol-2-yl)carbamate → tert-Butyl (4-propionylthiazol-2-yl)carbamate

HRID 32816Notes

Reaction equation

HRID 32816 reaction equation
[CH2:1]([Mg]Cl)[CH3:2].[C:5]([O:9][C:10](=[O:23])[NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17](=[O:22])N(OC)C)[N:16]=1)([CH3:8])([CH3:7])[CH3:6]>O1CCCC1>[C:5]([O:9][C:10](=[O:23])[NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17](=[O:22])[CH2:1][CH3:2])[N:16]=1)([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 58604314tert-Butyl (4-(methoxy(methyl)carbamoyl)thiazol-2-yl)carbamateHCID 178461633HCID 178461633, compound

Product 1

HCID 45117897tert-Butyl (4-propionylthiazol-2-yl)carbamateYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of ethyl magnesium chloride (126 mL, 0.252 mol, 2 M in tetrahydrofuran) was stirred and cooled to −70° C. on a dry ice/acetone bath. A solution of [4-(methoxy-methyl-carbamoyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (14.5 g, 0.0504 mol) in tetrahydrofuran (200 mL) was added dropwise over approximately 5 minutes. The mixture was stirred for 1 hour. The cooling bath was removed and stirring continued for an additional 2 hours. The mixture was poured into a mixture of ice and saturated aqueous ammonium chloride solution and then extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over magnesium sulfate and evaporated to give an off white solid which was purified by chromatography over a 350 g pad of silica gel eluted with 4:1 ethyl acetate/dichloromethane to afford (4-propionyl-thiazol-2-yl)-carbamic acid tert-butyl ester (7.09 g, 55%) as an off white solid.

Workup

  1. customThe cooling bath was removed
  2. stirringstirring
  3. waitcontinued for an additional 2 hours
  4. additionThe mixture was poured into a mixture of ice and saturated aqueous ammonium chloride solution
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto give an off white solid which
  10. customwas purified by chromatography over a 350 g pad of silica gel
  11. washeluted with 4:1 ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-f960c4b0c9e1442295160d1539d03a1e
Source dataset
uspto-grants-2008_09
Patent number
US07427635B2

Reaction notes

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