Triphenylphosphine → HCID 86731591, compound

HRID 1746415Notes

Reaction equation

[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=3[CH3:30])[CH2:19][CH:20]([CH3:22])[CH3:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:31])[O:4][N:3]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:65]1[CH2:70][CH2:69][CH2:68][CH2:67][CH:66]1[O:71][CH2:72][CH2:73]O>O1CCCC1>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:73][CH2:72][O:71][CH:66]4[CH2:67][CH2:68][CH2:69][CH2:70][O:65]4)=[CH:25][C:24]=3[CH3:30])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:31])[O:4][N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

An aliquot of tetrahydrofuran (THF) (1 mL) containing 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(4-hydroxy-2-methylphenyl)-N-isobutylbenzenesulfonamide (50 mg, 0.112 mmol) and DIAD (0.048 mL, 0.247 mmol) was added to triphenylphosphine (64.9 mg, 0.247 mmol). The reaction mixture was sealed and left to stir for 10 minutes before addition of 2-((tetrahydro-2H-pyran-2-yl)oxy)ethanol (0.015 mL, 0.112 mmol). The sealed reaction mixture was then heated to 50° C. over night. LCMS showed the formation of the product. LCMS (M+1) 572, RT 1.4 mins. Used without further purification in next reaction.

Workup

customThe reaction mixture was sealed
waitleft
customThe sealed reaction mixture
customLCMS (M+1) 572, RT 1.4 mins
customUsed without further purification
customin next reaction

Sources & evidence

ORD record: ord-88c1f65f54fd4d2ea12cec2ffd854b88
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150508B2

Reaction notes

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