Acetic Acid → HCID 23152690, compound

HRID 1012313Notes

Reaction equation

HRID 1012313 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:17][C:18]2[C:23]([C:24]=1[CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[CH:22][CH:21]=[C:20]([C:31]([O:33][CH3:34])=[O:32])[CH:19]=2.C([O-])(=O)C.[Na+].C(O)(=O)C.[Cl:44][CH2:45][C:46](Cl)=[O:47]>O1CCCC1.O>[CH2:9]([O:8][C:6]1[CH:5]=[CH:4][C:3]([C:16]2[NH:17][C:18]3[C:23]([C:24]=2[CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:22][CH:21]=[C:20]([C:31]([O:33][CH3:34])=[O:32])[CH:19]=3)=[C:2]([NH:1][C:46](=[O:47])[CH2:45][Cl:44])[CH:7]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6577Chloroacetyl chlorideHCID 517045Sodium AcetateHCID 23152596HCID 23152596, compound

Product 1

HCID 23152690HCID 23152690, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 2-(2-amino-4-benzyloxyphenyl)-3-cyclohexyl-1H-indole-6-carboxylate (6.17 g, 13.5 mmol), sodium acetate (1.22 g, 14.9 mmol) and acetic acid (0.86 ml, 14.9 mmol) in tetrahydrofuran (62 ml) was added dropwise chloroacetyl chloride (1.19 ml, 14.9 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 with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and methanol was added. The precipitated solid was collected by filtration, washed with methanol and dried in vacuo to give methyl 2-[4-benzyloxy-2-(2-chloroacetylamino)phenyl]-3-cyclohexyl-1H-indole-6-carboxylate (3.90 g, yield 54%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure and methanol
  6. additionwas added
  7. filtrationThe precipitated solid was collected by filtration
  8. washwashed with methanol
  9. customdried in vacuo

Sources & evidence

ORD record
ord-c9647dbc81394446ac5808caf3110993
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

Loading…