Diethyl Pyrocarbonate → HCID 57847220, compound

HRID 550310Notes

Reaction equation

HRID 550310 reaction equation
[NH:1]([C:8]([C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[C:16]([OH:18])=O)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])C.CCOC(OC(O[CH2:35][CH3:36])=O)=O.C(=O)([O-])O.[Na+]>CN(C=O)C>[C:2]1([NH:1][C:8]([C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]2[C:16]([N:21]2[C@@H:22]3[C@@H:23]([C@H:8]([C:36]4[CH:35]=[CH:15][CH:10]=[CH:11][CH:12]=4)[NH:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=43)[CH2:25][CH2:24]2)=[O:18])=[O:9])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 23013495HCID 23013495, compound

Product 1

HCID 57847220HCID 57847220, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of the compound (242 mg, 0.75 mmol) synthesized in Reference Example 8, (1S*,2R*)-2-(anilinocarbonyl)cyclohexanecarboxylic acid (222 mg, 0.90 mmol) and triethylamine (0.313 ml, 2.25 mmol) in DMF (7.5 ml) was added DEPC (0.151 ml, 0.90 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate solution was added, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (2:1, v/v). The title compound (1R*,2S*,3aR*,4R*,9bR*) (163 mg, 45%) was obtained as a white solid from the first eluted fraction.

Workup

  1. extractionthe reaction 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 under reduced pressure
  5. washeluted with hexane-ethyl acetate (2:1

Sources & evidence

ORD record
ord-51aead1eadf94093887d8d16d60bc1c9
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Reaction notes

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