Diethyl Pyrocarbonate → HCID 57847036, compound

HRID 735759Notes

Reaction equation

HRID 735759 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@H:18]3[CH2:19][CH2:20][NH:21][C@H:17]3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:10]2)=[CH:5][CH:4]=1.[C:22]([NH:30][C@@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@@H:32]1[C:37](O)=[O:38])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.CCOC(OC(OCC)=O)=O>CN(C=O)C>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@H:18]3[CH2:19][CH2:20][N:21]([C:37]([C@H:32]4[CH2:33][CH2:34][CH2:35][CH2:36][C@H:31]4[NH:30][C:22](=[O:29])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[O:38])[C@H:17]3[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 1268229(+)-cis-2-Benzamidocyclohexanecarboxylic AcidHCID 67150531HCID 67150531, compound

Product 1

HCID 57847036HCID 57847036, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of (3aS,4R,9bR)-4-[4-(methylthio)phenyl]-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinoline (1.10 g, 3.0 mmol) and (1S,2R)-2-(benzoylamino)cyclohexanecarboxylic acid (0.74 g, 3.0 mmol) in DMF (20 ml) were added under ice-cooling, triethylamine (0.91 g, 9.0 mmol), and then a solution of DEPC (0.49 g, 3.0 mmol) in DMF (5 ml). The reaction mixture was stirred at room temperature for 16 hrs., the reaction mixture was poured into ice water and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and eluted with hexane-ethyl acetate (2:1-1:1, v/v) to give N-[(1R,2S)-2-({(3aR,4R,9bR)-4-[4-(methylthio)phenyl]-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl}carbonyl)cyclohexyl]benzamide (0.45 g, 29%) from the first eluted fraction.

Workup

  1. additionwere added under ice-
  2. temperaturecooling
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure
  7. washeluted with hexane-ethyl acetate (2:1-1:1

Sources & evidence

ORD record
ord-ad7181e8f1104f4bbfae500e6f8aceb3
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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