Triphenylphosphine → HCID 91262502, compound

HRID 2087007Notes

Reaction equation

HRID 2087007 reaction equation
[C:1]([C:4]1[CH:8]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2F)[C:6](=[O:23])[C:5]=1[OH:24])(=[O:3])[CH3:2].[C:25]([O:35][CH3:36])(=[O:34])[C@H:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)O.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>C1COCC1>[C:1]([C:4]1[CH:8]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:6](=[O:23])[C:5]=1[O:24][C@H:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:25]([O:35][CH3:36])=[O:34])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 643570methyl (2S)-2-hydroxy-2-phenylacetateHCID 5363146Diisopropyl azodicarboxylateHCID 12093167HCID 12093167, compound

Product 1

HCID 91262502HCID 91262502, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) mixture of 4-acetyl-1-(4-chloro-2-fluorophenyl)-5-cyclohexyl-3-hydroxy-1,5-dihydro-2H-pyrrol-2-one (2.05 g, 5.84 mmol), methyl (S)-mandelate (1.36 g, 8.18 mmol) and triphenylphosphine (2.0 g, 7.6 mmol) in THF (50 ml) is added dropwise DIAD (1.6 ml, 7.6 mmol). The reaction is then left to warm to room temperature and is stirred for 12 hours. The solvent is removed under vacuum and the oily residue is plugged through a pad of silica gel (eluent 1/1 hexanes/ethyl acetate). The solvent is removed and the residual oil is purified by radial chromatography (eluent 9/1 hexanes/ethyl acetate) to yield each diastereomer (1 g) as a white foam.

Workup

  1. temperatureTo a cooled
  2. waitThe reaction is then left
  3. customThe solvent is removed under vacuum
  4. customThe solvent is removed
  5. customthe residual oil is purified by radial chromatography (eluent 9/1 hexanes/ethyl acetate)
  6. customto yield each diastereomer (1 g) as a white foam

Sources & evidence

ORD record
ord-348289e41a9244aebc8bd16f11bd7040
Source dataset
uspto-grants-2004_04
Patent number
US06727275B2

Reaction notes

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