Dicyclohexylcarbodiimide → HCID 178439347, compound

HRID 2392503Notes

Reaction equation

HRID 2392503 reaction equation
[F:1][C:2]1[CH2:7][CH2:6][CH:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]2)[CH2:4][CH:3]=1.[F:17][C:18]1[CH:23]=[C:22]([CH2:24][CH2:25][CH3:26])[CH:21]=[C:20]([F:27])[C:19]=1O.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[F:17][C:18]1[CH:23]=[C:22]([CH2:24][CH2:25][CH3:26])[CH:21]=[C:20]([F:27])[C:19]=1[O:15][C:14]([C@H:11]1[CH2:10][CH2:9][C@H:8]([CH:5]2[CH2:6][CH2:7][C:2]([F:1])=[CH:3][CH2:4]2)[CH2:13][CH2:12]1)=[O:16]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 18979655HCID 18979655, compoundHCID 178525694HCID 178525694, compound

Product 1

HCID 178439347HCID 178439347, compoundYield 112.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The crude product from b), 0.79 g of 1-fluoro-4-(trans-4-carboxycyclohexyl)cyclohex-l-ene, was cooled to 0°C. under nitrogen together with 0.66 g of 2,6-difluoro-4-propylphenol and 60 mg of dimethylaminopyridine in 10 ml of methylene chloride and treated within 45 minutes with a solution of 1.0 g of dicyclohexyl-carbodiimide in 5 ml of methylene chloride. After stirring at room temperature for 30 minutes the white suspension was filtered over a Celite/silica gel pad. The filtrate was evaporated completely and gave 1.5 g of trans-4-(1-fluoro-cyclohex- 1 -en-4-yl)cyclohexanecarboxylic acid 2,6-difluoro-4-propylphenyl ester, which gave 0.62 g of white crystals by repeated recrystallization from hexane. M.p. (C/N) 58.40°C., c.l.p. (N/I) 96.1°C.

Workup

  1. filtrationwas filtered over a Celite/silica gel pad
  2. customThe filtrate was evaporated completely

Sources & evidence

ORD record
ord-52c6728d975848abbf659ea62faa7bda
Source dataset
uspto-grants-1998_09
Patent number
US05800734

Reaction notes

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