1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57847051, compound

HRID 1009945Notes

Reaction equation

HRID 1009945 reaction equation
[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH:5]2[NH:12][CH2:13][CH2:14][CH:4]2[CH:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:21]([NH:29][C@@H:30]1[CH2:35][CH2:34][CH2:33][CH2:32][C@@H:31]1[C:36](O)=[O:37])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(=O)([O-])O.[Na+]>O1CCCC1.C(#N)C>[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C@@H:5]2[N:12]([C:36]([C@H:31]3[CH2:32][CH2:33][CH2:34][CH2:35][C@H:30]3[NH:29][C:21](=[O:28])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:37])[CH2:13][CH2:14][C@@H:4]2[C@@H:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 1268229(+)-cis-2-Benzamidocyclohexanecarboxylic AcidHCID 67150433HCID 67150433, compound

Product 1

HCID 57847051HCID 57847051, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-methyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline (130 mg, 0.48 mmol), (1S,2R)-2-(benzoylamino)cyclohexanecarboxylic acid (131 mg, 0.53 mmol), WSC (116 mg, 0.61 mmol), HOBt (97 mg, 0.63 mmol), acetonitrile (5 ml) and tetrahydrofuran (5 ml) was stirred at room temperature for 12 hrs. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried (over anhydrous Na2SO4), and the solvent was evaporated. The residue was subjected to column chromatography using silica gel (150 g) and eluted with hexane-ethyl acetate (4:1-1:1, v/v) to give the title compound (200 mg, 84%) as an amorphous form.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried (over anhydrous Na2SO4)
  4. customthe solvent was evaporated
  5. washeluted with hexane-ethyl acetate (4:1-1:1

Sources & evidence

ORD record
ord-49984cc9b837443783263c3c4dcc66be
Source dataset
uspto-grants-2011_07
Patent number
US07973163B2

Reaction notes

Loading…