Dichloromethane → HCID 67414948, compound

HRID 2389120Notes

Reaction equation

HRID 2389120 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

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 36987264-Isopropoxybenzeneboronic acidHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 67414948HCID 67414948, compoundYield 63.6%

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

  1. customThe flask was then purged with nitrogen
  2. customsealed
  3. stirringto stir for 16 hours
  4. customReaction
  5. temperaturewas then heated to 50° C. for two hours
  6. temperatureThe reaction mixture was then cooled to RT
  7. filtrationfiltrated
  8. customthe crude material was then purified via chromatography (SiO2, 40 g, 0-75% EtOAC/Hexane)

Sources & evidence

ORD record
ord-6bcc9c9e55dd4358a42fd63a9d2b5511
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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