Dicyclohexylcarbodiimide → HCID 18791999, compound

HRID 1005541Notes

Reaction equation

HRID 1005541 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][O:16][CH2:17][CH2:18][OH:19])[C:13]([CH3:20])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:24]([O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])(=[O:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O-])=[O:34].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:33]([O:19][CH2:18][CH2:17][O:16][CH2:15][N:14]1[C:10]([S:9][C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)=[C:11]([CH:21]([CH3:23])[CH3:22])[N:12]=[C:13]1[CH3:20])(=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:24]([O:37][CH2:38][CH2:39][Si:40]([CH3:41])([CH3:42])[CH3:43])=[O:36]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 4781802-[5-(3,5-Dimethyl-phenylsulfanyl)-4-isopropyl-2-methyl-imidazol-1-ylmethoxy]-ethanolHCID 17776726HCID 17776726, compound

Product 1

HCID 18791999HCID 18791999, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound 1 (334 mg, 1 mmol), 60 (303 mg, 1.00 mmol) and N,N-dimethylaminopyridine (122 mg, 1 mmol) in methylene chloride (5 mL) was added 1,3-dicyclohexylcarbodiimide (206 mg, 1.08 mmol) under ice-cooling. The reaction mixture was stirred at room temperature for 18 hours. The precipitated insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluate: hexane - ethyl acetate (1:1)) to give the compound 64 (580 mg, 94%) as oil. Rf 0.27 (1:1 EtOAc-hexane).

Workup

  1. temperaturecooling
  2. filtrationThe precipitated insoluble matter was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column (eluate: hexane - ethyl acetate (1:1))

Sources & evidence

ORD record
ord-b2a2070574fe4f4b8f31b30aaddbbd06
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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