Dicyclohexylcarbodiimide → HCID 54007225, compound

HRID 892391Notes

Reaction equation

HRID 892391 reaction equation
[CH3:1][O:2][C:3]([C@H:5]([O:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH3:6])=[O:4].[CH2:17]([O:29][C:30]1[CH:31]=[N:32][C:33]([C:36]2[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][CH:37]=2)=[N:34][CH:35]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][O:2][C:3]([C@H:5]([O:7][C:8]([C:9]1[CH:10]=[CH:11][C:12]([O:15][C:40](=[O:41])[C:39]2[CH:38]=[CH:37][C:36]([C:33]3[N:34]=[CH:35][C:30]([O:29][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:31][N:32]=3)=[CH:44][CH:43]=2)=[CH:13][CH:14]=1)=[O:16])[CH3:6])=[O:4]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 805700HCID 805700, compoundHCID 19895119HCID 19895119, compound

Product 1

HCID 54007225HCID 54007225, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

In a 50 ml round flask were charged 191 mg (0.85 mmol) of (R)-4-hydroxybenzoic acid 1-(methoxycarbonyl)-ethyl ester as prepared in Example 1-2), 360 mg (0.935 mmol) of 4-(5-dodecyloxypyrimidin-2-yl)benzoic acid, 10.4 mg (0.085 mmol) of N,N-dimethyl-4-aminopyridine, and 20 ml of methylene chloride, followed by stirring at 25 ° C. To the mixture was added 193 mg (0.935 mmol) of DCC to conduct a reaction at 25° C. for 18 hours. After completion of the reaction, the solid was removed by filtration, and the filtrate was washed successively three times with 10 ml portions of water, three times with 10 ml portions of a 5% acetic acid aqueous solution, and three times with 10 ml portions of water. The organic solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using a 20:1 (by volume) mixture of methylene chloride and diethyl ether. Recrystallization from hexane gave 110 mg (0.19 mmol) of Compound (35) in a yield of 22%.

Workup

  1. customa reaction at 25° C. for 18 hours
  2. customAfter completion of the reaction
  3. customthe solid was removed by filtration
  4. washthe filtrate was washed successively three times with 10 ml portions of water, three times with 10 ml portions of a 5% acetic acid aqueous solution, and three times with 10 ml portions of water
  5. customThe organic solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography
  7. additiona 20:1 (by volume) mixture of methylene chloride and diethyl ether
  8. customRecrystallization from hexane

Sources & evidence

ORD record
ord-9fd596be1a404ea7859e2c3f205329f8
Source dataset
uspto-grants-1992_06
Patent number
US05118442

Reaction notes

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