Phthalimide → HCID 58467996, compound

HRID 1879386Notes

Reaction equation

HRID 1879386 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:45][C:46]1[C:51]([F:52])=[CH:50][CH:49]=[CH:48][C:47]=1[C@@H:53]1[CH2:63][CH2:62][C@H:61](O)[C:56]2=[N:57][CH:58]=[CH:59][CH:60]=[C:55]2[C@H:54]1[NH:65][C:66](=[O:72])[O:67][C:68]([CH3:71])([CH3:70])[CH3:69]>C(Cl)Cl>[F:45][C:46]1[C:51]([F:52])=[CH:50][CH:49]=[CH:48][C:47]=1[C@@H:53]1[CH2:63][CH2:62][C@@H:61]([N:19]2[C:15](=[O:25])[C:16]3[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:18]2=[O:20])[C:56]2=[N:57][CH:58]=[CH:59][CH:60]=[C:55]2[C@H:54]1[NH:65][C:66](=[O:72])[O:67][C:68]([CH3:70])([CH3:69])[CH3:71]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58468018HCID 58468018, compound

Product 1

HCID 58467996HCID 58467996, compoundYield 113.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIAD (0.356 mL, 1.832 mmol) was added to a methylene chloride (5 mL) solution of phthalimide (0.270 g, 1.832 mmol), triphenylphosphine (0.481 g, 1.832 mmol) and tert-butyl (5S,6S,9S)-6-(2,3-difluorophenyl)-9-hydroxy-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (0.358 g, 0.916 mmol) at 0° C. The reaction was gradually warmed up to room temperature and stirred at room temperature for 3 days. Volatile components were removed in vacuo and the crude residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed two more times with water before being dried (sodium sulfate), filtered and concentrated. Flash chromatography using ethyl acetate in hexane from 0 to 45% gave the desired product (0.541 g, ca 80% purity, 90% for 2 steps): MS(ESI)[M+H+]=520.16.

Workup

  1. customVolatile components were removed in vacuo
  2. customthe crude residue was partitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed two more times with water
  4. dry with materialbefore being dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6a164d383bb24091adfdf3537eeb445f
Source dataset
uspto-grants-2012_11
Patent number
US08314117B2

Reaction notes

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