Water → HCID 59923442, compound

HRID 2297715Notes

Reaction equation

HRID 2297715 reaction equation
C([S:4][CH2:5][CH2:6][N:7]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:8](=[O:21])[NH:9][C@@H:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12])(=O)C.O.C(OCC)(=O)C>N>[SH:4][CH2:5][CH2:6][N:7]([CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:8](=[O:21])[NH:9][C@@H:10]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 86586956HCID 86586956, compound

Product 1

HCID 59923442HCID 59923442, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

(2S)-2-[3-[2-(Acetylthio)ethyl]-3-phenethylureido]-3-phenylpropionic acid (Compound No. 7-30, 646 mg) is dissolved in 28% aqueous ammonia (15 ml) under a nitrogen atmosphere, and the solution is stirred at room temperature for one hour. To the reaction mixture are added water and ethyl acetate, and the aqueous layer is separated from the organic layer. To the aqueous layer is added 6 N hydrochloric acid under ice cooling to acidify it, and the whole is extracted with ethyl acetate. The organic layer is washed with water and saturated brine successively, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting oily matter is purified by silica gel column chromatography to give 415 mg (81%) of the titled compound (Compound No. 11-1).

Workup

  1. customthe aqueous layer is separated from the organic layer
  2. additionTo the aqueous layer is added 6 N hydrochloric acid under ice cooling
  3. extractionthe whole is extracted with ethyl acetate
  4. washThe organic layer is washed with water and saturated brine successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oily matter is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-59aab5f80f794b80bb6cbb187ce9e2f6
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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