Hydrochloric Acid → (E)-1-[2-(Boc-Amino-)-4-methylthiazol-5-yl]-3-(dimethylamino)prop-2-en-1-one

HRID 416281Notes

Reaction equation

HRID 416281 reaction equation
[C:1]([N:8](C(OC(C)(C)C)=O)[C:9]1[S:10][C:11]([C:15](=[O:21])/[CH:16]=[CH:17]/[N:18]([CH3:20])[CH3:19])=[C:12]([CH3:14])[N:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[O-].[Na+].[OH-].[Na+].Cl>CO>[C:1]([NH:8][C:9]1[S:10][C:11]([C:15](=[O:21])/[CH:16]=[CH:17]/[N:18]([CH3:19])[CH3:20])=[C:12]([CH3:14])[N:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 58930666(E)-1-[2-(bis-Boc-Amino)-4-methylthiazol-5-yl]-3-(dimethylamino)prop-2-en-1-one

Product 1

HCID 58930506(E)-1-[2-(Boc-Amino-)-4-methylthiazol-5-yl]-3-(dimethylamino)prop-2-en-1-oneYield 110.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of enamino ketone 337 (859 mg, 2.09 mmol) in methanol (12 mL) was treated with NaOMe solution (25% ww, 1.9 ml). The reaction mixture refluxed for 24 hours, treated with NaOH solution (1M, 3 ml), cooled to the room temperature, carefully neutralized (pH 7.5-8) with 1M HCl and extracted with EtOAc. Extract was dried over MgSO4, filtered and evaporated to provide a residue corresponding to the title compound (721 mg, more than quantitative yield), which was used for the next step without further purification. MS (m/z): 311.40 (calc) 312.1 (MH+) (found).

Workup

  1. temperatureThe reaction mixture refluxed for 24 hours
  2. extractionextracted with EtOAc
  3. extractionExtract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-33afc8e0c88f483dbf787508c40ea93d
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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