Dicyclohexylcarbodiimide → HCID 86757837, compound

HRID 276767Notes

Reaction equation

HRID 276767 reaction equation
[C:1]([O:9][CH2:10][C:11]1[C:23]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[CH:14]=[CH:13][CH:12]=1)(=[O:8])[CH2:2][CH2:3][CH2:4][C:5]([O-:7])=[O:6].[F:24][C:25]1[C:30](O)=[C:29]([F:32])[C:28]([F:33])=[C:27]([F:34])[C:26]=1[F:35].C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[F:24][C:25]1[C:30]([O:6][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][C:1]([O:9][CH2:10][C:11]2[C:23]3[CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]=3[CH:14]=[CH:13][CH:12]=2)=[O:8])=[C:29]([F:32])[C:28]([F:33])=[C:27]([F:34])[C:26]=1[F:35]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 18546646HCID 18546646, compound

Product 1

HCID 86757837HCID 86757837, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
20 °C

Procedure

Fluorenylmethyl glutarate (2.5 kg) (prepared as described in Step 4) and pentafluorophenol (1.63 kg) were dissolved in ethyl acetate (25 L). The solution was treated with a solution of dicyclohexylcarbodiimide (1.83 kg) in ethyl acetate (7.5 L) and the mixture was stirred at 20° C. overnight. The resulting slurry was filtered and the solids were washed through with ethyl acetate (10 L). The filtrate was evaporated at atmospheric pressure to a volume of 7.5 L and diluted with hexane (75 L). The slurry was filtered at 60-65° C. then allowed to cool to room temperature and stirred overnight. The slurry was cooled to 0° C. for 1 hour, the solid collected by filtration and washed with 10:1 hexane/ethyl acetate (15 L). The solid was dried in vacuo at 45° C. to afford the title compound as a white crystalline solid.

Workup

  1. filtrationThe resulting slurry was filtered
  2. washthe solids were washed through with ethyl acetate (10 L)
  3. customThe filtrate was evaporated at atmospheric pressure to a volume of 7.5 L
  4. additiondiluted with hexane (75 L)
  5. filtrationThe slurry was filtered at 60-65° C.
  6. temperatureto cool to room temperature
  7. stirringstirred overnight
  8. temperatureThe slurry was cooled to 0° C. for 1 hour
  9. filtrationthe solid collected by filtration
  10. washwashed with 10:1 hexane/ethyl acetate (15 L)
  11. customThe solid was dried in vacuo at 45° C.

Sources & evidence

ORD record
ord-319a42f113d541688bf43a20e2b19ec7
Source dataset
uspto-grants-2002_03
Patent number
US06355611B1

Reaction notes

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