Ammonia → HCID 59923467, compound

HRID 2297713Notes

Reaction equation

HRID 2297713 reaction equation
C([S:8][CH2:9][CH:10]([N:20]([CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:21](=[O:41])[NH:22][C@@H:23]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:24]([O:26]CC1C=CC=CC=1)=[O:25])[CH2:11][S:12]CC1C=CC=CC=1)C1C=CC=CC=1.N.C(=O)=O.CO.[Na].[Cl-].[NH4+]>O1CCCC1>[SH:8][CH2:9][CH:10]([N:20]([CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:21](=[O:41])[NH:22][C@@H:23]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:24]([OH:26])=[O:25])[CH2:11][SH:12]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 21973728Carbon dioxide methanolHCID 86586954HCID 86586954, compound

Product 1

HCID 59923467HCID 59923467, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl (2S)-2-[3-[2-(benzylthio)-1[(benzylthio)methyl]ethyl]-3-phenethylureido]-3-phenylpropionate (Compound No. 1-72, 996 mg) in anhydrous tetrahydrofuran (20 ml) is added dropwise to liquid ammonia (80 ml) under a nitrogen atmosphere and dry ice-methanol cooling. Then, metallic sodium (300 mg) by portions is added thereto until coloration does not disappear, and the mixture is stirred as it is for one hour. Ammonium chloride by portions is added to the reaction mixture to decolorize it, and then a nitrogen gas is bubbled through the mixture at room temperature to evaporate ammonia. To the resulting residue is added 1 N hydrochloric acid 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 magnesium sulfate and concentrated under reduced pressure to give the titled compound (Compound No. 9-1).

Workup

  1. customa nitrogen gas is bubbled through the mixture at room temperature
  2. customto evaporate ammonia
  3. additionTo the resulting residue is added 1 N hydrochloric acid
  4. extractionthe whole is extracted with ethyl acetate
  5. washThe organic layer is washed with water and saturated brine successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-07dcca054a0745019588581594cf0d46
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

Loading…