Dichloromethane → HCID 67414948, compound
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.[CH:19]([O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)([CH3:21])[CH3:20].C(Cl)Cl.C(N(CC)CC)C>>[CH:19]([O:22][C:23]1[CH:28]=[CH:27][C:26]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C@:12]2([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]2)[CH:6]=[CH:5]3)=[CH:25][CH:24]=1)([CH3:21])[CH3:20]Participants
Procedure
(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (3 g, 0.01 mol), 4-isopropoxyphenylboronic acid (5 g, 0.03 mol), and cupric acetate (2.55 g, 0.0140 mol) were placed in a vial followed by methylene chloride (100 mL, 2 mol) and finally triethylamine (9.78 mL, 0.0702 mol) at 23° C. The flask was then purged with nitrogen, sealed and stirred at room temperature overnight. The reaction was allowed to stir for 16 hours. Reaction was then heated to 50° C. for two hours. The reaction mixture was then cooled to RT and filtrated and the crude material was then purified via chromatography (SiO2, 40 g, 0-75% EtOAC/Hexane) to give 2.4 g of the desired product as a colorless solid. Material was used without additional purification. ESI-MS: 378 (M+H)+
Workup
- customThe flask was then purged with nitrogen
- customsealed
- stirringto stir for 16 hours
- customReaction
- temperaturewas then heated to 50° C. for two hours
- temperatureThe reaction mixture was then cooled to RT
- filtrationfiltrated
- customthe crude material was then purified via chromatography (SiO2, 40 g, 0-75% EtOAC/Hexane)
Sources & evidence
- ORD record
- ord-4d6ce0ecc54744e29d0fc6b386e04263
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546359B2
Reaction notes
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