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

HRID 1769364Notes

Reaction equation

HRID 1769364 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

HCID 815143,3-Dimethylbutanoyl chlorideHCID 38061142,3-DihydroxybutanedioateHCID 6451240Aluminum(III) ChlorideHCID 18947552Methyl 3-[5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

Product 1

HCID 18947551Methyl 3-[3-(3,3-dimethyl-1-oxo-1-butyl)-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethyl-propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. extractionThe product was extracted with EtOAc
  2. washthe organic layer was washed successively with 0.5M NaK tartrate, H2O, and brine
  3. customThe solvent was then removed
  4. customyellow/orange oil (3.5 g) was used without purification in the following step

Sources & evidence

ORD record
ord-a0a9eee35b7145ffba562983962077c0
Source dataset
uspto-grants-1995_01
Patent number
US05380850

Reaction notes

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