Benzoyl chloride → HCID 53792042, compound

HRID 1735407Notes

Reaction equation

HRID 1735407 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][CH2:11][C:12]([C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]([C@@H:21]1[CH2:25][CH2:24][CH2:23][N:22]1[C:26]([NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)=[O:27])=[O:20])=[O:13].S([O-])(O)(=O)=O.[K+]>N1C=CC=CC=1>[C:1]([O:10][CH2:11][C:12]([C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:19]([C@@H:21]1[CH2:25][CH2:24][CH2:23][N:22]1[C:26]([NH:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)=[O:27])=[O:20])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 516920Potassium bisulfateHCID 54003774HCID 54003774, compound

Product 1

HCID 53792042HCID 53792042, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzoyl chloride (0.17 ml) was added to a pyridine solution (4.5 ml) of (S)-2-[[(S)-2-(hydroxyacetyl)-1-pyrrolidinyl]carbonyl]-N-[(4-methylphenyl)methyl]-1-pyrrolidinecarboxamide (0.46 g) obtained in Example 10, and the mixture was stirred under ice-cooling for 4 hours. The reaction mixture was poured into saturated potassium hydrogensulfate and extracted with methylene chloride. The extract was washed with saturated sodium hydrogencarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated to give the title compound (0.37 g) (see Table 2).

Workup

  1. temperaturecooling for 4 hours
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with saturated sodium hydrogencarbonate and water in order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bac82d2acbac4266b4f089e09a8b7057
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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