Phosphorus oxychloride → (s)-2-(2-Phenyl-1-(5-phenyloxazol-2-yl)ethyl)isoindoline-1,3-dione

HRID 1524859Notes

Reaction equation

HRID 1524859 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C@@H:12]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]([NH:15][CH2:16][C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14].P(Cl)(Cl)(Cl)=O>CN(C=O)C>[C:26]1([CH2:25][C@H:12]([N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])[C:13]2[O:14][C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][N:15]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66674794(s)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-n-(2-oxo-2-phenyl-ethyl)-3-phenyl-propionamide

Product 1

HCID 14824564(s)-2-(2-Phenyl-1-(5-phenyloxazol-2-yl)ethyl)isoindoline-1,3-dioneYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 48 Part A (412 mg, 1 mmol) was dissolved in DMF and treated with phosphorous oxychloride (460 mg, 3 mmol) at 90° C. according to the procedure described by Robert Dow et al. (J. Org. Chem., 1990, 55, 386) to yield 160 mg (41% yield) of the product. MS 395.2 (M+H)+.

Sources & evidence

ORD record
ord-460a07d05fe349fabdedb1d07b6a9a7d
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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