Diethyl Ether → HCID 21310531, compound

HRID 583409Notes

Reaction equation

HRID 583409 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:39])[CH2:7][CH2:8][CH2:9][CH:10]([N:21]([C:23](=[O:38])[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=1)[CH3:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)C.C(OCC)C>O.O1CCCC1>[F:36][C:34]([F:35])([F:37])[C:26]1[CH:25]=[C:24]([CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=1)[C:23]([N:21]([CH:10]([CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[CH2:9][CH2:8][CH2:7][C:6]([OH:39])=[O:5])[CH3:22])=[O:38]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 57082339HCID 57082339, compound

Product 1

HCID 21310531HCID 21310531, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 108 mg (1.93 mmol) of potassium hydroxide in 1 ml of water is added at room temperature to a solution of 970 mg (1.84 mmol) of 5-[(3,5-bistrifluoromethyl-benzoyl)-N-methyl-amino]-6-(1H-indol-3-yl)-hexanoic acid ethyl ester in 10 ml of tetrahydrofuran. The mixture is stirred at room temperature for 18 hours and then 10 ml of water and 20 ml of diethyl ether are added. The aqueous phase is separated off and rendered acidic with 6N hydrochloric acid. Ethyl acetate is then added and the product is extracted. The combined organic phases are washed with brine, dried over magnesium sulfate and concentrated by evaporation. The title compound crystallises out from diethyl ether/hexane in the form of white crystals. M.p.: 152-157° C.; MS (EI): 500 (M+.), 370, 241, 229,130; TLC: (ethyl acetate/acetic acid 99:1) Rf =0.49.

Workup

  1. customThe aqueous phase is separated off
  2. additionEthyl acetate is then added
  3. extractionthe product is extracted
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. customThe title compound crystallises out from diethyl ether/hexane in the form of white crystals

Sources & evidence

ORD record
ord-cbfa44706ea24694b88f0d08394c7bdc
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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