1,2-Dichloroethane → Coumarin
Reaction equation
C(Cl)CCl.CC1=CCCC(C)=CC[C@:13]2(C)[C:25](=[O:26])[C:24](O)=[C:23]([C@@H:28]([CH2:30][OH:31])C)[C@H:14]2[CH2:15][CH:16]=C(C)[C@@H](O)CC1.C(C(CCCCN)C(O)=O)(OC(C)(C)C)=O.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[O:26]1[C:25]2[C:24](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:23]=[CH:28][C:30]1=[O:31]Participants
Procedure
EDC (1.0 mg, 0.0052 mmol) and DMAP (0.64 mg, 0.0052 mmol) were added to a stirred solution of terpestacin (2.0 mg, 0.005 mmol) and Boc-6-aminohexanoic acid (1.2 mg, 0.0052 mmol) in DMF (2 mL) at 0° C. The reaction mixture was reacted overnight at room temperature. The reaction product was extracted with ethanol (4 mL×3), treated with 20% TFA in CH2Cl2 (1 mL) and stirred at room temperature for 2 hours. DIPEA (1.3 mg, 0.01 mmol) and 6-((7-amino-4-methylcoumarin-3-acetyl)amino)hexanoic acid succinimidyl ester (2.2 mg, 0.005 mmol, MOLECULAR PROBES®) were added thereto at 0° C. After being stirred at room temperature for 4 hours, the reaction product was extracted with ethanol (20 mL) and purified by TLC (CH2Cl2:MeOH=10:1) to obtain coumarin-conjugated terpestacin (yield: 61%). The synthesized coumarin-conjugated terpestacin is depicted in Formula 4.
Workup
- customThe reaction mixture was reacted overnight at room temperature
- extractionThe reaction product was extracted with ethanol (4 mL×3)
- additiontreated with 20% TFA in CH2Cl2 (1 mL)
- customat 0° C
- stirringAfter being stirred at room temperature for 4 hours
- extractionthe reaction product was extracted with ethanol (20 mL)
- custompurified by TLC (CH2Cl2:MeOH=10:1)
Sources & evidence
- ORD record
- ord-848f3d465b344ecbb7855cd72231d4e4
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450502B2
Reaction notes
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