Acetic Acid → HCID 58679113, compound

HRID 1442550Notes

Reaction equation

HRID 1442550 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[C:16]1[NH:20][C:19]2[CH:21]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[S:23][C:18]=2[C:17]=1[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C([O-])(=O)C.[Na+].C(O)(=O)C.[Cl:43][CH2:44][C:45](Cl)=[O:46]>O1CCCC1.O>[CH2:9]([O:8][C:6]1[CH:5]=[CH:4][C:3]([C:16]2[NH:20][C:19]3[CH:21]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[S:23][C:18]=3[C:17]=2[CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[C:2]([NH:1][C:45](=[O:46])[CH2:44][Cl:43])[CH:7]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6577Chloroacetyl chlorideHCID 517045Sodium AcetateHCID 58679084HCID 58679084, compound

Product 1

HCID 58679113HCID 58679113, compoundYield 110.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 5-(2-amino-4-benzyloxyphenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (6.30 g, 13.8 mmol), sodium acetate (1.36 g, 16.6 mmol) and acetic acid (0.95 ml, 16.6 mmol) in tetrahydrofuran (100 ml) was added dropwise chloroacetyl chloride (1.32 ml, 16.6 mmol), and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution, saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The obtained crude product of methyl 5-[4-benzyloxy-2-(2-chloroacetylamino)phenyl]-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (8.22 g) was used for Step 6 without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution, saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d71ff88977d24db38df1525024a94b9d
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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