HCID 22279872, compound → HCID 22279728, compound

HRID 2086182Notes

Reaction equation

HRID 2086182 reaction equation
C[O:2][C:3]([NH:5][C:6]([CH3:17])([CH2:9][CH2:10][C:11]1[S:12][C:13]([Br:16])=[CH:14][CH:15]=1)[CH2:7][OH:8])=O.CC(C)([O-])C.[K+]>CN(C)C=O>[Br:16][C:13]1[S:12][C:11]([CH2:10][CH2:9][C:6]2([CH3:17])[CH2:7][O:8][C:3](=[O:2])[NH:5]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 22279872HCID 22279872, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22279728HCID 22279728, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methoxycarbonylamino-2-methyl-4-(5-bromothiophen-2-yl)butan-1-ol (12.4 g, 38.6 mmol) obtained in Example 1(e) was dissolved in dimethylformamide (125 ml), and potassium t-butoxide (6.50 g, 57.9 mmol) was added thereto in an ice bath under a nitrogen atmosphere followed by stirring for 3 hours at the same temperature. The reaction mixture was poured into ice-cold 10% hydrochloric acid (300 ml), and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was concentrated in vacuo, and the residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=4 1-1:2) to afford the title compound (10.7 g, 95% yield) as a white crystalline solid.

Workup

  1. customin an ice bath under a nitrogen atmosphere followed
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent was concentrated in vacuo
  6. customthe residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=4 1-1:2)

Sources & evidence

ORD record
ord-9d90180e373a47729eabdba36fd605f9
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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