Ammonium Chloride → 5-(6-Chloro-2-hexyl-indol-1-yl)-3(R)-methyl-5-oxo-pentanoic acid methyl ester

HRID 2406671Notes

Reaction equation

HRID 2406671 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[NH:8]2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl[C:24](=[O:33])[CH2:25][C@@H:26]([CH3:32])[CH2:27][C:28]([O:30][CH3:31])=[O:29].[Cl-].[NH4+]>C(Cl)Cl.C1COCC1.C(OCC)(=O)C>[CH3:31][O:30][C:28](=[O:29])[CH2:27][C@H:26]([CH3:32])[CH2:25][C:24]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)[CH:6]=[C:7]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:33]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 105858626-chloro-2-hexyl-1H-indoleHCID 23665647Potassium tert-butoxideHCID 86665257(S)-methyl 5-chloro-3-methyl-5-oxopentanoate

Product 1

HCID 666440215-(6-Chloro-2-hexyl-indol-1-yl)-3(R)-methyl-5-oxo-pentanoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the cold solution of 6-Chloro-2-hexyl-1H-indole in methylene chloride was added solution of potassium tert-butoxide in THF and stirred for 30 minutes. Then (S)-methyl 5-chloro-3-methyl-5-oxopentanoate in methylene chloride was added to the reaction mixture and was stirred for 3 hours. The reaction mixture was then treated with saturated ammonium chloride and ethyl acetate. The product was purified by column chromatography.

Workup

  1. stirringwas stirred for 3 hours
  2. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-7fb90f4407034ea6ac0129605af36f07
Source dataset
uspto-grants-2014_08
Patent number
US08809382B2

Reaction notes

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