Triethylamine → HCID 91296289, compound

HRID 2266896Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[NH2:11][CH:12]([CH:17]1[CH2:22][CH:21]2[CH:19]([C:20]2([F:24])[F:23])[CH2:18]1)[C:13]([O:15][CH3:16])=[O:14].C(N(CC)CC)C.CCOC(C)=O.CCCCCC>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:11][CH:12]([CH:17]2[CH2:18][CH:19]3[CH:21]([C:20]3([F:23])[F:24])[CH2:22]2)[C:13]([O:15][CH3:16])=[O:14])(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

5-Chlorothiophene-2-sulfonyl chloride (1.26 g, 4.82 mmol) was added dropwise (5 min) as a solution in CH2Cl2 (10 mL) to a 0° C. solution of methyl amino(6,6-difluorobicyclo[3.1.0]hex-3-yl)acetate (0.9 g, 4.38 mmol) in CH2Cl2 (10 mL) and triethylamine (1.22 mL, 8.77 mmol). The solution was allowed to warm to 25° C. overnight (19 h). An aliquot was taken and TLC (1:4 EtOAc-hexane) indicated that the reaction was complete. It was diluted in CH2Cl2 (100 mL) and the organic layer was washed with 1N HCl (20 mL) and saturated aqueous NaCl (20 mL). The organic layer was dried over MgSO4, filtered, and concentrated to obtain a crude off-yellow solid (1.69 g). The crude product was purified by the Biotage Flash™ 40 chromatography instrument, eluent: 1:4 EtOAc-hexanes, to afford methyl {[(5-chlorothien-2-yl)sulfonyl]amino}(6,6-difluorobicyclo[3.1.0]hex-3-yl)acetate as a colorless oil (0.230 g, 12.23%). Mass Spectrum (−ESI): 384 (M+H)+.

Workup

washthe organic layer was washed with 1N HCl (20 mL) and saturated aqueous NaCl (20 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customto obtain a crude off-yellow solid (1.69 g)
customThe crude product was purified by the Biotage Flash™ 40 chromatography instrument, eluent

Sources & evidence

ORD record: ord-32fb876160a34e318816f7173f860a63
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858658B2

Reaction notes

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