Triphenylphosphine → HCID 131730605, compound

HRID 2098329Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][C:21]1[CH:22]=[C:23]([CH:28]=[C:29]([O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[O:39][C:40]([CH3:43])=[N:41][N:42]=3)=[CH:34][CH:33]=2)[CH:30]=1)[C:24]([O:26][CH3:27])=[O:25].CC(OC(/N=N/C(OC(C)C)=O)=O)C.[CH3:58][O:59][CH2:60][C@H:61](O)[CH3:62]>C1(C)C=CC=CC=1>[CH3:58][O:59][CH2:60][C@@H:61]([O:20][C:21]1[CH:22]=[C:23]([CH:28]=[C:29]([O:31][C:32]2[CH:33]=[CH:34][C:35]([C:38]3[O:39][C:40]([CH3:43])=[N:41][N:42]=3)=[CH:36][CH:37]=2)[CH:30]=1)[C:24]([O:26][CH3:27])=[O:25])[CH3:62]

Participants

Conditions

Temperature: 90 °C

Procedure

Triphenyl phosphine (21 g, 80 mmol, 2.8 equiv.) was added to a stirring solution of Methyl 3-hydroxy-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate (Intermediate 7) (9.3 g, 28.52 mmol, 1 equiv.) in toluene (100 mL) under nitrogen atmosphere at room temperature. The mixture was heated to 90° C. for 30 min. A mixture of Diisopropylazadicarboxylate (DIAD) (11.52 g, 57 mmol, 2 equiv.) and (R)-(−)-1-Methoxy-propan-2-ol (3.8 g, 42.8 mmol, 1.5 equiv.) in toluenene (50 mL) was added to the above reaction mixture at 90° C. and the reaction mixture was stirred for 3 h at 100° C. The completion of the reaction was monitored by TLC. After completion, the reaction mixture was concentrated under vacuum and purified by column chromatography to get (5)-Methyl 3-[(1-methoxypropan-2-yl)oxy]-5-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy]benzoate (Intermediate 8) as thick liquid (27 g). Sodium hydroxide (3.43 g, 85.92 mmol, 3 equiv.) in water (55 mL) was added to a stirring solution of (9-Methyl 3-[(1-methoxypropan-2-yl)oxy]-5-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy]benzoate (crude) (Intermediate 8) in methanol (110 mL) in round bottomed flask. The reaction mixture was stirred at room temperature for 2 h. The reaction was monitored by TLC. After completion, methanol was removed under vacuum and water was added. The reaction mixture was filtered. Filtrate was washed with ethyl acetate. The aqueous layer was acidified and extracted with DCM twice. The combined organic layer was washed with water, brine and dried over anhydrous sodium sulphate, filtered and concentrated in vacuum to furnish title acid as thick liquid (9.5 g).

Workup

additionwas added to the above reaction mixture at 90° C.
concentrationAfter completion, the reaction mixture was concentrated under vacuum
custompurified by column chromatography

Sources & evidence

ORD record: ord-ca709370ea1747ac9d718f72c3cff27b
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450494B2

Reaction notes

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