(Diethylamino)sulfur trifluoride → HCID 86702080, compound

HRID 873594Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3(O)[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[O:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(S(F)(F)[F:44])CC)C>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3([F:44])[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[O:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

tert-Butyl 4-(4-(1-((benzyloxy)carbonyl)azetidine-3-carboxamido)phenyl)-4-hydroxypiperidine-1-carboxylate (2.5 g, 4.91 mmol) in 50 mL dichloromethane was cooled to −78° C. and diethylaminosulfur trifluoride was added dropwise via a syringe. The reaction solution was stirred at −78° C. for an additional 1 hour and then warmed to 0° C. The reaction was allowed to stir at 0° C. for 1 hour and was cooled back down to −78° C. The reaction mixture was diluted with 50 mL of dichloromethane followed by quenching with 10 mL methanol. The solution was washed with saturated sodium bicarbonate and brine, dried with magnesium sulfate and filtered. Concentration and normal phase chromatography provided the title compound.

Workup

temperaturewarmed to 0° C
stirringto stir at 0° C. for 1 hour
temperaturewas cooled back down to −78° C
customby quenching with 10 mL methanol
washThe solution was washed with saturated sodium bicarbonate and brine
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationConcentration and normal phase chromatography

Sources & evidence

ORD record: ord-3054564f6c2e49b8b1bc570cf9256152
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975398B2

Reaction notes

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