Dicyclohexylcarbodiimide → HCID 12773843, compound

HRID 2058937Notes

Reaction equation

HRID 2058937 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([N:6]1[C@@H:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[CH2:12][CH2:11][C@H:7]1[C:8](O)=[O:9])=[O:5].C(=O)=O.CC(C)=O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([C@H:13]2[N:6]3[C@@H:7]([C:8](=[O:9])[S:1][CH2:2][CH2:3][C:4]3=[O:5])[CH2:11][CH2:12]2)[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 12773838HCID 12773838, compoundHCID 18522661Acetone cardice

Product 1

HCID 12773843HCID 12773843, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The compound produced in Example 2 is dissolved in about 500 milliliters methylene chloride and the solution is chilled under nitrogen to 15° C. in a dry ice-acetone mixture. 4-Dimethylaminopyridine is added and the mixture is stirred for five minutes. A slight excess of dicyclohexylcarbodiimide dissolved in methylene chloride is added with stirring. The chilled source is removed after 15 minutes and the solution is stirred overnight at room temperature. The volume of the reaction mixture is reduced on a rotary evaporator under reduced pressure to about 100 milliliters. A precipitate is removed by filtration and the filter residue is washed several times with methylene chloride. The filtrate and combined washings are washed successively with 1N HCl, saturated aqueous NaHCO3, water and saline and the solution is dried over MgSO4. Evaporation of the methylene chloride with a rotary evaporator under reduced pressure yields the title compound.

Workup

  1. additionis added
  2. stirringwith stirring
  3. customThe chilled source is removed after 15 minutes
  4. stirringthe solution is stirred overnight at room temperature
  5. customThe volume of the reaction mixture is reduced on a rotary evaporator under reduced pressure to about 100 milliliters
  6. customA precipitate is removed by filtration
  7. washthe filter residue is washed several times with methylene chloride
  8. washare washed successively with 1N HCl, saturated aqueous NaHCO3, water and saline
  9. dry with materialthe solution is dried over MgSO4
  10. customEvaporation of the methylene chloride
  11. customwith a rotary evaporator under reduced pressure

Sources & evidence

ORD record
ord-a38f20e1ba75411ba341261454f0ca79
Source dataset
uspto-grants-1982_03
Patent number
US04320057

Reaction notes

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