Triphenylphosphine → HCID 23400759, compound

HRID 1062911Notes

Reaction equation

HRID 1062911 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([O:17][C:18]([NH:20][C:21]1([CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([OH:45])[CH:40]=3)=[CH:34][C:33]=2[Cl:46])[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23][CH2:22]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[Cl:47][C:48]1[CH:49]=[C:50]([CH:53]=[C:54]([Cl:56])[CH:55]=1)[CH2:51]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C1COCC1>[C:13]([O:17][C:18]([NH:20][C:21]1([CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([O:45][CH2:51][C:50]4[CH:49]=[C:48]([Cl:47])[CH:55]=[C:54]([Cl:56])[CH:53]=4)[CH:40]=3)=[CH:34][C:33]=2[Cl:46])[CH2:22][O:23][C:24]([CH3:28])([CH3:27])[O:25][CH2:26]1)=[O:19])([CH3:14])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 432363,5-Dichlorobenzylic alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23400760HCID 23400760, compound

Product 1

HCID 23400759HCID 23400759, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.31 mL) was added to a THF solution (5 mL) containing the compound of Example 106 (650 mg), 3,5-dichlorobenzyl alcohol (350 mg), triphenylphosphine (530 mg). The mixture was stirred for 18 hours. Subsequently, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic phase was sequentially washed with water and a saturated aqueous solution of sodium chloride and was dried with anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain the desired product (440 mg) as a colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was sequentially washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride and was dried with anhydrous sodium sulfate
  4. customThe solvent was then removed by distillation under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f821d28ff0b84a669d712a74dba46c47
Source dataset
uspto-grants-2005_11
Patent number
US06963012B2

Reaction notes

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