Triphenylphosphine → HCID 86708924, compound

HRID 1522077Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][S:14]([NH:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:16])=[O:15].[CH3:24][CH:25]([CH2:28]O)[CH2:26]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>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[S:14](=[O:15])(=[O:16])[N:17]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:26][CH:25]([CH3:28])[CH2:24]1

Participants

Conditions

Temperature: -20 °C

Procedure

Ethyl 2-((N-(2,6-dichloro-4-(trifluoromethyl)phenyl)sulfamoyl)amino)acetate (300 mg, 0.76 mmol), 2-methylpropane-1,3-diol (75 mg, 0.76 mmol) and triphenylphosphine (498 mg, 1.90 mmol) were dissolved in anhydrous THF (30 mL), and then cooled down −20° C. after removal of air in the reactor by purging nitrogen gas. DIAD (384 mg, 1.90 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 (225 mg, 66%, light yellow solid). 1H NMR (300 MHz, CDCl3): δ 7.65 (s, 1H), 7.63 (s, 1H), 4.44-4.38 (m, 1H), 4.30-4.17 (m, 2H), 4.11-4.03 (m, 1H), 3.98-3.87 (m, 2H), 3.53-3.44 (m, 1H), 3.24-3.17 (m, 1H), 2.59 (m, 1H), 1.31 (t, 3H, J=7.1 Hz), 0.94 (d, 3H, J=6.7 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-72241148ba6a423599dac303e8db3150
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073906B2

Reaction notes

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