Phthalimide → HCID 57826475, compound

HRID 1960977Notes

Reaction equation

HRID 1960977 reaction equation
O[CH2:2][C@@H:3]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([F:14])([F:13])[F:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:42]1(=[O:52])[NH:46][C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]12.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:47]=[C:45]1[C:44]2[C:43](=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:42](=[O:52])[N:46]1[CH2:2][C@@H:3]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 57826474HCID 57826474, compound

Product 1

HCID 57826475HCID 57826475, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-dimethylethyl ((1S)-2-hydroxy-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)carbamate (4.2 g, 13.2 mmol), triphenylphosphine (4.5 g, 17.1 mmol) and phthalimide (1.9 g, 13.2 mmol) in THF (66 mL) at 25° C. was added diethyl azodicarboxylate (2.7 mL, 17.1 mmol). After stirring at RT for 1 h, the reaction solution was concentrated under vacuum and the residue purified on silica gel (1% MeOH in DCM) affording the title compound (3.2 g, 54%) as a white solid: LCMS (ES) m/z 449 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated under vacuum
  2. customthe residue purified on silica gel (1% MeOH in DCM)

Sources & evidence

ORD record
ord-1ac018b4e83b4ab38aedfa50ddcf44d0
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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