3,3-Dimethylbutanoyl chloride → Methyl 3-[3-(3,3-dimethyl-1-oxo-1-butyl)-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethyl-propanoate
Reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]([CH3:12])([CH3:11])[CH2:7][C:8](Cl)=[O:9].[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[CH2:23][O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([CH2:34][C:35]([CH3:41])([CH3:40])[C:36]([O:38][CH3:39])=[O:37])=[CH:28]2.C(C(C(C([O-])=O)O)O)([O-])=O>C(Cl)Cl>[CH3:5][C:6]([CH3:12])([CH3:11])[CH2:7][C:8]([C:28]1[C:27]2[C:31](=[CH:32][CH:33]=[C:25]([O:24][CH2:23][C:14]3[CH:15]=[CH:16][C:17]4[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:13]=3)[CH:26]=2)[NH:30][C:29]=1[CH2:34][C:35]([CH3:41])([CH3:40])[C:36]([O:38][CH3:39])=[O:37])=[O:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of AlCl3 (5.7 g, 42 mmol) in CH2Cl2 (30 mL) at 0° C. was added 3,3-dimethylbutanoyl chloride (2.4 mL. 17 mmol). After 15 minutes at 0° C., a solution of the ester from step C (3.0 g, 7.7 mmol) in CH2Cl2 (10 mL) was added by double-tipped needle. The mixture was stirred a further 20 minutes, at which point it was poured into a mixture of 0.5M Na, K tartrate (150 mL) and ice (100 g). The product was extracted with EtOAc, and the organic layer was washed successively with 0.5M NaK tartrate, H2O, and brine. The solvent was then removed and yellow/orange oil (3.5 g) was used without purification in the following step.
Workup
- extractionThe product was extracted with EtOAc
- washthe organic layer was washed successively with 0.5M NaK tartrate, H2O, and brine
- customThe solvent was then removed
- customyellow/orange oil (3.5 g) was used without purification in the following step
Sources & evidence
- ORD record
- ord-4cf50b56211a4dc09b1bc0e15b3f5056
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05272145
Reaction notes
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