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Water → Methyl 4-[6-(2-ethylhexanamido)indol-1-ylmethyl]-3-methoxybenzoate

HRID 1904459
Notes
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Reaction equation

HRID 1904459 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=2[O:22][CH3:23])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:31]([CH:33]([CH2:37][CH2:38][CH2:39][CH3:40])[C:34](Cl)=[O:35])[CH3:32].O>C(Cl)Cl.C(OCC)(=O)C>[CH2:31]([CH:33]([CH2:37][CH2:38][CH2:39][CH3:40])[C:34]([NH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=2[O:22][CH3:23])=[CH:4][CH:3]=1)=[O:35])[CH3:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 791032-Ethylhexanoyl chlorideHCID 14708762Methyl 4-(6-aminoindol-1-ylmethyl)-3-methoxybenzoate

Product 1

HCID 20038737Methyl 4-[6-(2-ethylhexanamido)indol-1-ylmethyl]-3-methoxybenzoateYield 99%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of methyl ester (B) (0.5 g) in methylene chloride (16 ml) was cooled to 0° C. and treated with triethylamine (0.34 ml) followed by 2-ethylhexanoyl chloride (0.31 ml). The resulting solution was stirred at 0° C. for 15 minutes and then at room temperature for 30 minutes. The mixture was diluted with ethyl acetate and poured into cold water. The organic layer was washed sequentially with 10% v/v hydrochloric acid, water, and brine; dried (MgSO4) and evaporated. The residue was purified by flash chromatography on a 4×18 cm silica gel column using 35:65 v/v ethyl acetate:hexane as the eluent to give methyl 4-[6-(2-ethylhexanamido)indol-1-ylmethyl]-3-methoxybenzoate (C) (0.7 g; 99%) as a white solid; partial NMR: 0.9(t, 6H, 2CH3), 1.5(m, 9H).

Workup

  1. waitat room temperature for 30 minutes
  2. washThe organic layer was washed sequentially with 10% v/v hydrochloric acid, water, and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography on a 4×18 cm silica gel column

Sources & evidence

ORD record
ord-cb4cecfb6362403db8992f1b99b82c05
Source dataset
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04837235

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes