HCID 67771027, compound → HCID 67771609, compound

HRID 1720534Notes

Reaction equation

HRID 1720534 reaction equation
C(OC([N:8]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:9][C:10]([N:12]1[CH2:35][CH2:34][CH2:33][C@H:13]1[C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[CH:21]([OH:32])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)=[O:15])=[O:11])=O)(C)(C)C>Cl.O1CCOCC1>[OH:32][CH:21]([C@@H:17]1[CH2:18][CH2:19][CH2:20][N:16]1[C:14](=[O:15])[C@@H:13]1[CH2:33][CH2:34][CH2:35][N:12]1[C:10](=[O:11])[CH2:9][NH:8][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1

Participants

3

Reactant 1

HCID 67771027HCID 67771027, compound

Product 1

HCID 67771609HCID 67771609, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

(2S)-1-{N-[N-(tert-Butoxycarbonyl)-N-phenylglycyl]-L-prolyl}-2-[1-hydroxy-2-(4-methoxyphenoxy)ethyl]pyrrolidine (656 mg) was dissolved in 4N hydrochloric acid/1,4-dioxane (5 ml) and the mixture was stirred at room temperature for 0.5 hour. The reaction mixture was concentrated, and the resultant residue was dissolved in saturated aqueous sodium bicarbonate, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give 518 mg of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe resultant residue was dissolved in saturated aqueous sodium bicarbonate
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-54ebbcab514644ff83c21f0a2681e5a1
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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