Phthalimide → HCID 57826903, compound

HRID 1845365Notes

Reaction equation

HRID 1845365 reaction equation
CC([N:5]([C@H:9]([CH2:19]O)[CH2:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=1[F:18])[C:6](=[O:8])[O-:7])(C)C.[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.C1(P([C:45]2[CH:50]=[CH:49]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:51]COC(/N=N/C(OCC)=O)=O>O1CCCC1.CO>[F:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([F:18])[C:11]=1[CH2:10][C@H:9]([NH:5][C:6](=[O:8])[O:7][C:50]([CH3:49])([CH3:45])[CH3:51])[CH2:19][N:25]1[C:21](=[O:31])[C:22]2[C:23](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:24]1=[O:26]

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86633543HCID 86633543, compound

Product 1

HCID 57826903HCID 57826903, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 200 mL round-bottomed flask was added 1,1-dimethylethyl[(1S)-2-(2,6-difluorophenyl)-1-(hydroxymethyl)ethyl]carbamate (3.38 g, 11.76 mmol), phthalimide (2.02 g, 13.73 mmol), and PS TPP (Polymer bound TriphenylPhosphine (2.15 mmol/g, 4.92 g, 14.76 mmol) in Tetrahydrofuran (THF) (58.8 ml). DEAD (2.23 ml, 14.09 mmol) was added and the mixture stirred at ambient temperature for approximately 30 minutes at which point MeOH was added. The mixture was filtered through Celite adsorbed onto silica and purified via column chromatography affording the title compound (2.7 g, 55%): LC-MS (ES) m/z=317 (M+H)+.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered through Celite
  3. custompurified via column chromatography

Sources & evidence

ORD record
ord-8e1769f82f0d47348625bb92ee875779
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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