HCID 86717846, compound → HCID 86717845, compound

HRID 591060Notes

Reaction equation

HRID 591060 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]([CH3:23])[C:13](=[O:22])[S:14][C:15]=3[CH:16]([OH:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:10][C:5]=2[CH:4]=[CH:3][CH2:2]1>ClCCl.C(Br)(C)(C)C.[Ag]=O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]([CH3:23])[C:13](=[O:22])[S:14][C:15]=3[CH:16]([O:21][C:5]([CH3:10])([CH3:6])[CH3:4])[C:17]([O:19][CH3:20])=[O:18])=[CH:10][C:5]=2[CH:4]=[CH:3][CH2:2]1

Participants

5

Reactant 1

HCID 86717846HCID 86717846, compound

Product 1

HCID 86717845HCID 86717845, compoundYield 58.4%

Reagents, catalysts & solvents 3

HCID 92152Silver(II) oxideCatalystHCID 6344DichloromethaneSolventHCID 10485t-Butyl bromideSolvent

Procedure

At room temperature, a solution of methyl (4-1-benzopyran-6-yl-3-methyl-2-oxo-2,3-dihydro-thiazol-5-yl)-hydroxy-acetate (33d) (84 mg, 0.25 mmol) and silver oxide (580 mg, 2.5 mmol) in dichloromethane (500 μL) and tert-butyl bromide (5 mL) was stirred for 8 hours. The mixture was then filtered and concentrated. The crude product was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 90/10) to afford the desired product (33e) as a white solid (29 mg, 0.073 mmol, 29%).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated
  3. customThe crude product was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 90/10)

Sources & evidence

ORD record
ord-9d510b87c4a8446e9aa031e1018dd5d9
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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