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Water → N-{(1R,2S)-2-[(3aR*,4R*,9bR*)-(5-Acetyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl)carbonyl]cyclohexyl}benzamide

HRID 550311
Notes
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Reaction equation

HRID 550311 reaction equation
[C:1]1([C@H:7]2[C@H:16]3[CH2:17][CH2:18][N:19]([C:20]([C@H:22]4[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]4[NH:28][C:29](=[O:36])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:21])[C@H:15]3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:44](Cl)(=[O:46])[CH3:45].O>C(Cl)(Cl)Cl>[C:44]([N:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[C@@H:15]2[N:19]([C:20]([C@H:22]3[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]3[NH:28][C:29](=[O:36])[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[O:21])[CH2:18][CH2:17][C@H:16]2[C@@H:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:46])[CH3:45]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57846915HCID 57846915, compound

Product 1

HCID 68981617N-{(1R,2S)-2-[(3aR*,4R*,9bR*)-(5-Acetyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl)carbonyl]cyclohexyl}benzamideYield 46.1%

Reagents, catalysts & solvents

1
HCID 6212ChloroformSolvent

Procedure

The compound (130 mg, 0.27 mmol) of Example 1 and triethylamine (69 mg, 0.30 mmol) were dissolved in chloroform (2 ml), acetyl chloride (99 mg, 0.33 mmol) was added under ice-cooling, and the mixture was stirred at room temperature for 1 hr. and at 60° C. for 2 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried (over anhydrous MgSO4), and the solvent was evaporated. The residue was subjected to column chromatography using silica gel (150 g), and eluted with hexane-ethyl acetate (3:1-0:1, v/v) to give the title compound (65 mg, 46%) as an amorphous form.

Workup

  1. temperaturecooling
  2. waitand at 60° C. for 2 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried (over anhydrous MgSO4)
  6. customthe solvent was evaporated
  7. washeluted with hexane-ethyl acetate (3:1-0:1

Sources & evidence

ORD record
ord-ea96d154682b4cceb414abd0a324b65e
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07943770B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes