Triphenylphosphine → HCID 86708917, compound

HRID 1522069Notes

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].[CH2:21]=[C:22]([CH2:25]O)[CH2:23]O.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>[CH2:21]=[C:22]1[CH2:25][N:10]([C:3]2[C:4]([Cl:9])=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[S:11](=[O:13])(=[O:12])[N:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:23]1

Participants

Conditions

Temperature: -20 °C

Procedure

Ethyl 2-((N-(2,4,6-trichlorophenyl)sulfamoyl)amino)acetate (300 mg, 0.83 mmol), 2-methylenepropane-1,3-diol (73 mg, 0.83 mmol) and triphenylphosphine (544 mg, 2.08 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 (420 mg, 2.08 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 (305 mg, 89%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.40 (s, 2H), 5.25 (s, 1H), 5.16 (s, 1H), 4.36 (s, 2H), 4.27-4.20 (m, 4H), 4.08 (s, 2H), 1.33-1.28 (t, 3H, J=7.1, 7.1 Hz).

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-51fd7e18369d4dfd90c8c37b2ba93562
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073906B2

Reaction notes

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