Dicyclohexylcarbodiimide → HCID 20290363, compound

HRID 1413706Notes

Reaction equation

HRID 1413706 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([N:6]1[CH:15]([C:16]([OH:18])=O)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5].C(=O)=O.CC(C)=O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:16]1(=[O:18])[CH:15]2[N:6]([CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[CH2:14]2)[C:4](=[O:5])[CH2:3][CH2:2][S:1]1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1324722-(3-Sulfanylpropanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 18522661Acetone cardice

Product 1

HCID 20290363HCID 20290363, 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 chilling 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 1 N, 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 a white solid which is recrystallized from diethyl ether to yield the title compound.

Workup

  1. additionis added
  2. stirringwith stirring
  3. customThe chilling 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 1 N, 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
  12. customyields a white solid which
  13. customis recrystallized from diethyl ether

Sources & evidence

ORD record
ord-86b4fef1fb1144b99c62a63ffbb814c3
Source dataset
uspto-grants-1981_02
Patent number
US04251444

Reaction notes

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