Triphenylphosphine → HCID 86708920, compound

HRID 1522072Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][S:11]([NH:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:13])=[O:12].[C:21]1([CH2:26]O)([CH2:24]O)[CH2:23][CH2:22]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[O:12]=[S:11]1(=[O:13])[N:10]([C:3]2[C:4]([Cl:9])=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH2:26][C:21]2([CH2:23][CH2:22]2)[CH2:24][N:14]1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

Conditions

Temperature: -20 °C

Procedure

Ethyl 2-((N-(2,4,6-trichlorophenyl)sulfamoyl)amino)acetate (380 mg, 1.05 mmol), cyclopropane-1,1-diyldimethanol (107 mg, 1.05 mmol) and triphenylphosphine (689 mg, 2.63 mmol) were dissolved in anhydrous THF (30 mL) in a reactor, and then cooled down −20° C. after removal of air in the reactor by purging nitrogen gas. DIAD (532 mg, 2.63 mmol) was dropwisely added to the reaction mixture and agitated for 5 hr at room temperature. The resultant was concentrated under reduced pressure and purified by column chromatography (dichloromethane:hexane:ethyl acetate=5:4:1), finally yielding the title compound (198 mg, 44%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.39 (s, 2H), 4.39 (s, 2H), 4.26-4.19 (q, 2H, J=7.1, 7.1, 7.1 Hz), 3.73 (s, 2H), 3.57 (s, 2H), 1.32-1.27 (t, 3H, J=7.1, 7.1 Hz), 0.66-0.64 (m, 4H).

Workup

customafter removal of air in the reactor
customby purging nitrogen gas
concentrationThe resultant was concentrated under reduced pressure
custompurified by column chromatography (dichloromethane:hexane:ethyl acetate=5:4:1)

Sources & evidence

ORD record: ord-1f1b34be3ff54bdcb42f4ca48c69d4cf
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073906B2

Reaction notes

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