Phthalimide → HCID 71006879, compound

HRID 403348Notes

Reaction equation

HRID 403348 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:19][CH2:18][C@H:17](O)[C:12]2=[N:13][CH:14]=[CH:15][N:16]=[C:11]2[C@H:10]1[NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25].[C:29]1(=[O:39])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31](=[O:38])[NH:30]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl.C(OCC)(=O)C.CCCCCC>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:19][CH2:18][C@@H:17]([N:30]2[C:31](=[O:38])[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:29]2=[O:39])[C:12]2=[N:13][CH:14]=[CH:15][N:16]=[C:11]2[C@H:10]1[NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:27])[CH3:25]

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 71006874HCID 71006874, compound

Product 1

HCID 71006879HCID 71006879, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

In an oven-dried 100 mL round-bottomed flask was dissolved tert-butyl (5S,6S,9S)-6-(2,3-difluorophenyl)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyrazin-5-ylcarbamate (35.3 mg, 0.090 mmol) (9, azeotroped with dry benzene) in methylene chloride (3 mL) to give a colorless solution. isoindoline-1,3-dione (26.5 mg, 0.180 mmol) and triphenylphosphine (47.3 mg, 0.180 mmol) were added, followed by diisopropylazodicarboxylate (0.026 mL, 0.135 mmol). The mixture was stirred at rt under nitrogen. After 22 h, the mixture was directly subject to flash column chromatography up to 50% ethyl acetate/hexane afforded one major peak. Concentration afforded the desired product as a colorless oil. 1H NMR indicated that some elimination product might also be present. This was carried onto next reaction without further purification and characterization.

Workup

  1. customto give a colorless solution
  2. customafforded one major peak
  3. concentrationConcentration

Sources & evidence

ORD record
ord-0a4ccf71df5d463c897626d1051086f0
Source dataset
uspto-grants-2014_06
Patent number
US08748429B2

Reaction notes

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