Dicyclohexylcarbodiimide → HCID 59534303, compound

HRID 562929Notes

Reaction equation

HRID 562929 reaction equation
[F:1][C:2]([F:16])([F:15])[C@@:3]([O:13][CH3:14])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5].[F:17][C:18]1[C:23](O)=[C:22]([F:25])[C:21]([F:26])=[C:20]([F:27])[C:19]=1[F:28].C1CCC(N=C=NC2CCCCC2)CC1>CC#N>[F:1][C:2]([F:15])([F:16])[C@@:3]([O:13][CH3:14])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([O:6][C:23]1[C:22]([F:25])=[C:21]([F:26])[C:20]([F:27])=[C:19]([F:28])[C:18]=1[F:17])=[O:5]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 2723917(+)-Mosher's acid

Product 1

HCID 59534303HCID 59534303, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

(R)-(+)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid (Mosher Acid) (936 mg, 3.9 mmol) and pentafluorophenol (1.10 g, 6.0 mmol) were stirred in anhydrous MeCN (6 mL) and cooled to 0° C. DCC (803 mg, 3.9 mmol) was added at one portion and the reaction mixture was stirred at 0° C. for 1 h and then allowed to warm to rt and stirred for additions 16 h. The suspension was filtered and washed with cold MeCN. The filtrated were evaporated and dried on high vacuum. The crude product was purified by column chromatography (20:1=PE: EtOAc) to yield 4 as a colourless oil (1.52 g, 97%; Campbell et al., J. Org. Chem., 1995, 60, 4602).

Workup

  1. temperatureto warm to rt
  2. stirringstirred for additions 16 h
  3. filtrationThe suspension was filtered
  4. washwashed with cold MeCN
  5. customThe filtrated were evaporated
  6. customdried on high vacuum
  7. customThe crude product was purified by column chromatography (20:1=PE: EtOAc)

Sources & evidence

ORD record
ord-7ebda6c622e045f5885be28195da0631
Source dataset
uspto-grants-2011_11
Patent number
US08067424B2

Reaction notes

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