Diisopropylcarbodiimide → 6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-hexanoic Acid Pentafluorophenyl Ester

HRID 20905

Reaction equation

HRID 20905 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].C(N=C=NC(C)C)(C)C.[F:29][C:30]1[C:35](O)=[C:34]([F:37])[C:33]([F:38])=[C:32]([F:39])[C:31]=1[F:40]>ClCCl>[F:29][C:30]1[C:35]([O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]2=[O:1])=[C:34]([F:37])[C:33]([F:38])=[C:32]([F:39])[C:31]=1[F:40]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 13041PentafluorophenolHCID 781851,3-Dihydro-1,3-dioxo-2H-isoindole-2-hexanoic acid

Product 1

HCID 593472896-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-hexanoic Acid Pentafluorophenyl EsterYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Referring to scheme 12, compound 41a (13.3 g, 51 mmol) was dissolved in anhydrous dichloromethane (40 mL) and cooled to 0° C. under argon. To the solution were added diisopropyl carbodiimide (6.31 g, 7.7 mL, 50 mmol) and pentafluoro phenol (42, 9.2 g, 50 mmol). After overnight the reaction mixture was evaporated to dryness. To the residue ethyl acetate (100 mL) was added and the filtered to remove diisopropyl urea. The precipitate was washed with ethyl acetate (50 mL). The combined organic layer was washed with saturated sodium bicarbonate and water. The organic layer was dried over sodium sulfate, filtered and evaporated to dryness. Compound 43a (Rf=0.8 in 10% EtOAc/Hexane, 21.65 g, 92%) was obtained, which was directly used for the next step without further purification.

Workup

  1. customAfter overnight the reaction mixture was evaporated to dryness
  2. additionTo the residue ethyl acetate (100 mL) was added
  3. filtrationthe filtered
  4. customto remove diisopropyl urea
  5. washThe precipitate was washed with ethyl acetate (50 mL)
  6. washThe combined organic layer was washed with saturated sodium bicarbonate and water
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-943b155b15a6447a8e8a5b8587520e9e
Source dataset
uspto-grants-2010_06
Patent number
US07745608B2

Linked notes

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