Ammonia → HCID 86586955, compound

HRID 2297714Notes

Reaction equation

HRID 2297714 reaction equation
[SH:1][CH2:2][CH:3]([N:6]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:7](=[O:20])[NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])[CH2:4][SH:5].N>CO>[S:1]1[CH2:2][CH:3]([N:6]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:7](=[O:20])[NH:8][C@@H:9]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:10]([OH:12])=[O:11])[CH2:4][S:5]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59923467HCID 59923467, compound

Product 1

HCID 86586955HCID 86586955, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S)-2-[3-[2-Mercapto-1-(mercaptomethyl)ethyl]-3-phenethylureido]-3-phenylpropionic acid (Compound No. 9-1, 780 mg) is dissolved in methanol (2 ml). To the solution are added 1 N aqueous ammonia (10 ml) and a 1% aqueous ferric chloride solution (0.5 ml), and the mixture is stirred at room temperature for two hours while bubbling air through it. The reaction mixture is concentrated under reduced pressure, 2 N hydrochloric acid is added to the concentrate 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 514 mg (66%) of the titled compound (Compound No. 10-1) as oily matter.

Workup

  1. customwhile bubbling air through it
  2. concentrationThe reaction mixture is concentrated under reduced pressure, 2 N hydrochloric acid
  3. additionis added to the
  4. concentrationconcentrate under ice cooling
  5. extractionthe whole is extracted with ethyl acetate
  6. washThe organic layer is washed with water and saturated brine successively
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting oily matter is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d405554953804932ae37a693866a865f
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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