Structure of 6-(Tritylthio)hexanoic acid
CAS No.: 80441-55-0
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 80441-55-0 |
Formula : | C25H26O2S |
M.W : | 390.54 |
SMILES Code : | O=C(O)CCCCCSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3 |
MDL No. : | MFCD11226801 |
InChI Key : | ILAPAFBLFPIIBL-UHFFFAOYSA-N |
Pubchem ID : | 21480969 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20℃; for 12h; | Compound 69 was synthesized from compound 43 (FIG. 13A). 6-Tritylsulfanyl-hexanoic acid was coupled to 43 via standard EDC/HOBt coupling. To a solution of 43 (140 mg, 34 mumol) and 6-tritylsulfanyl-hexanoic acid (67 mg, 5 equivalents) in dichloromethane (2 mL) was added hydroxybenzotriazole (23 mg, 5 equivalents) and triethlamine (24 muL, 5 equivalents). The solution was cooled to ice bath temperature and 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide(EDC) (33 mg, 5 equivalents) was added. The solution was allowed to warm to room temperature and stirred at this temperature for 12 hours. The reaction mixture was diluted with dichloromethane (10 mL) and decanted into water (10 mL). The aqueous phase was extracted with dichloromethane (3×20 mL). The combined organic layers were then washed with 1 N aqueous hydrochloric acid (3×30 mL), saturated aqueous bicarbonate solution (1×30 mL) and brine (1×10 mL). The solution was dried over magnesium sulfate and concentrated. Flash column chromatography (DCM/MeOH 10:1) gave the intermediate product as a colorless foam shaped solid. (145 mg, 96%) |