Triethylamine → HCID 59737195, compound
Reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)[CH:2]=1.[NH2:25][C:26]1[CH:31]=[C:30]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)[CH:29]=[CH:28][C:27]=1[NH:37]C(=O)OC(C)(C)C.C(N(CC)CC)C>S(Cl)(Cl)=O.CN(C=O)C>[NH2:37][C:27]1[CH:28]=[CH:29][C:30]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)=[CH:31][C:26]=1[NH:25][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([NH:7][C:3]1[CH:2]=[C:1]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=1)=[O:18]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Acid 183 (0.103 g, 0.32 mmol) in thionyl chloride (3 mL) with a few drops of DMF was stirred at room temperature for 15 min then concentrated, diluted with dry THF (10 mL), cooled to 0° C. then treated with amine 4 (0.12 g, 0.41 mmol) and triethylamine (0.086 mL, 0.61 mmol). The reaction mixture was stirred at 0° C. for 30 min then quenched with aqueous NH4Cl, extracted with AcOEt, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (eluent: 50% AcOEt-hexane) to give the title compound 184 (0.111 g, 52% yield).
Workup
- concentrationthen concentrated
- additiondiluted with dry THF (10 mL)
- customthen quenched with aqueous NH4Cl
- extractionextracted with AcOEt
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography (eluent: 50% AcOEt-hexane)
Sources & evidence
- ORD record
- ord-241631d01e57491fb4649b8b3f889573
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598168B2
Reaction notes
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