Triphenylphosphine → HCID 86617926, compound

HRID 1161583Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:32])[N:4]=[C:5]([S:30][CH3:31])[C:6]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([OH:28])[C:21]=1[F:29])=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1.[Si:33]([O:40][CH2:41][C@H:42](O)[CH3:43])([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3](=[O:32])[N:4]=[C:5]([S:30][CH3:31])[C:6]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][C@@H:42]([CH3:43])[CH2:41][O:40][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C:21]=1[F:29])=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: -78 °C

Procedure

[2-(2-Fluoro-3-hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene]carbamic acid methyl ester (Example (3d), 275 mg), (R)-1-(t-butyldimethylsilanyloxy)propan-2-ol [CAS No. 136918-07-5] (171 mg), and triphenylphosphine (236 mg) were dissolved in 3 ml of THF under a nitrogen atmosphere, and the resulting mixture was cooled to −78° C. After the addition of 0.177 ml of N,N′-diisopropylazodicarboxylate, the mixture was allowed to warm to room temperature with stirring overnight. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (heptane-ethyl acetate) to give the title compound (343 mg).

Workup

temperatureto warm to room temperature
concentrationThe reaction mixture was concentrated
customthe residue was purified by silica gel column chromatography (heptane-ethyl acetate)

Sources & evidence

ORD record: ord-4b2f0b8514444205a2fb2940736284df
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

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