Triphenylphosphine → HCID 90449477, compound

HRID 1411269Notes

Reaction equation

[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([S:17](Cl)(=O)=O)[CH:15]=3)[N:10]([C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([SH:17])[CH:15]=3)[N:10]([C:21](=[O:26])[C:22]([F:24])([F:25])[F:23])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

The 1′-acetyl-1-(2,2,2-trifluoroacetyl)spiro[indoline-3,3′-pyrrolidine]-5-sulfonyl chloride (101 mg, 0.25 mmol) obtained as an intermediate in Step 2 of Example 236 was dissolved in tetrahydrofuran (3 mL). Thereafter, water (0.1 mL) and triphenylphosphine (0.23 g, 0.86 mmol) were added to the above obtained solution, and the thus obtained mixture was then stirred at 50° C. for 4 hours. Thereafter, the reaction solution was diluted with water, and was then extracted with ethyl acetate. The organic layer was washed with brine, and was then dried over anhydrous magnesium sulfate, followed by concentration in vacuo. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=20:1) to obtain 1-(1′-acetyl-5-mercaptospiro[indoline-3,3′-pyrrolidin]-1-yl)-2,2,2-trifluoroethanone (26 mg, 31%) in the form of a colorless oily product.

Workup

extractionwas then extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialwas then dried over anhydrous magnesium sulfate
concentrationfollowed by concentration in vacuo
customThe obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record: ord-23c39c1b3ff64b98a008fec3a9a45f49
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921576B2

Reaction notes

Loading…