Tetrahydrofuran → 3-(2-{(3,3,3-Triphenylpropanoyl)amino}acetylamino)propionic acid

HRID 272063Notes

Reaction equation

HRID 272063 reaction equation
[C:1]1([C:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][C:9]([NH:11][CH2:12][C:13]([NH:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])=[O:14])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.[OH-].[Na+]>CO>[C:29]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:8][C:9]([NH:11][CH2:12][C:13]([NH:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:14])=[O:10])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22647252Ethyl 3-(2-{(3,3,3-triphenylpropanoyl)amino}acetylamino)propionate

Product 1

HCID 110045083-(2-{(3,3,3-Triphenylpropanoyl)amino}acetylamino)propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.7 Grams of ethyl 3-(2-{(3,3,3-triphenylpropanoyl)amino}-acetylamino)propionate was dissolved in a mixed liquid consisting of 70 ml of tetrahydrofuran and 20 ml of methanol. To the solution 5.0 ml of 4N aqueous sodium hydroxide solution was added at room temperature, followed by an hour's stirring at the same temperature. The reaction liquid was distilled off under reduced pressure, and the residue was rendered acidic by addition of 1N hydrochloric acid, extracted with ethyl acetate, washed with saturated saline solution and dried over anhydrous magnesium sulfate. Upon distilling the solvent off under reduced pressure, 1.10 g of the title compound was obtained.

Workup

  1. waitfollowed by an hour
  2. customThe reaction liquid
  3. distillationwas distilled off under reduced pressure
  4. additionthe residue was rendered acidic by addition of 1N hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washwashed with saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationUpon distilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-181cd92028a840b18daf66aba7e0c94f
Source dataset
uspto-grants-2008_11
Patent number
US07452908B2

Reaction notes

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