Phthalimide → (4R)-4-(4,5-diphenyloxazol-2-yl)-4-phthalimido-1-butene

HRID 1741390Notes

Reaction equation

HRID 1741390 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C@@H:18](O)[CH2:19][CH:20]=[CH2:21])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]([C@H:18]([N:27]3[C:26](=[O:28])[C:25]4=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]4[C:23]3=[O:33])[CH2:19][CH:20]=[CH2:21])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 56991674(4S)-4-(4,5-diphenyloxazol-2-yl)-4-hydroxy-1-butene

Product 1

HCID 54558309(4R)-4-(4,5-diphenyloxazol-2-yl)-4-phthalimido-1-buteneYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4S)-4-(4,5-diphenyloxazol-2-yl)-4-hydroxy-1-butene (9.2 g) in THF (100 ml) were added phthalimide (7.0 g) and triphenylphosphine (12.5 g) and diethyl azodiformate (7.5 ml) at room temperature. The mixture was stirred for 2 hours at room temperature and partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl, water, sat. NaHCO3 and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give (4R)-4-(4,5-diphenyloxazol-2-yl)-4-phthalimido-1-butene (9.7 g). MS (m/z): 421 (M+ +1) IR (Nujol): 1760, 1710 cm-1NMR (CDCl3, δ): 3.1-3.4 (2H, m), 5.0-5.3 (2H, m), 5.63 (1H, dd, J=6.0, 10.0 Hz), 5.7-6.0 (1H, m), 7.2-8.0 (14H, m) HPLC; chiralcel OD, 10% isopropanol/hexane, 32.2 ml/min

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with 1N-HCl, water, sat. NaHCO3 and brine
  3. customThe dried solvent was evaporated in vacuo
  4. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b8dedd3f334c42c884813e90c64a6806
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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