(Diethylamino)sulfur trifluoride → HCID 118253466, compound

HRID 921892Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[C:9]1[C:10]([Cl:29])=[C:11]([C:17]2(O)[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]2)[CH:12]=[C:13]([C:15]#[N:16])[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:45])CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[C:9]1[C:10]([Cl:29])=[C:11]([C:17]2([F:45])[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]2)[CH:12]=[C:13]([C:15]#[N:16])[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 3-(3-((tert-butoxycarbonyl)(4-methoxybenzyl)amino)-2-chloro-5-cyanophenyl)-3-hydroxyazetidine-1-carboxylate (408 mg, 0.75 mmol) in dry CH2Cl2 (12 mL) at −78° C. under nitrogen was added diethylaminosulfur trifluoride (153 μL, 0.90 mmol). The mixture was allowed to warm to 0° C. over 4 h and quenched by adding 1M aqueous NaOH at −5° C. The reaction mixture was diluted with EtOAc, washed with water, brine, and dried over sodium sulfate. Solvent was removed. The residue was purified by ISCO column (12 g) chromatography, eluting with hexane containing 0 to 40% EtOAc to afford tert-butyl 3-(3-((tert-butoxycarbonyl)(4-methoxybenzyl)amino)-2-chloro-5-cyanophenyl)-3-fluoroazetidine-1-carboxylate (321 mg).

Workup

customquenched
additionby adding 1M aqueous NaOH at −5° C
additionThe reaction mixture was diluted with EtOAc
washwashed with water, brine
dry with materialdried over sodium sulfate
customSolvent was removed
customThe residue was purified by ISCO column (12 g) chromatography
washeluting with hexane containing 0 to 40% EtOAc

Sources & evidence

ORD record: ord-fe18b8e4cdcf4853bd8bb5a595d31722
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273057B2

Reaction notes

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