Hydrochloric Acid → (S)-2-[[(S)-2-(Hydroxy-2-(p-methoxyphenoxy)ethyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

HRID 1735398Notes

Reaction equation

HRID 1735398 reaction equation
Cl.C(O[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[CH:14](O)[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[O:8])(C)(C)C.[NH:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1C(O)=O.[CH2:34]([N:41]=[C:42]=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CN(C=[O:48])C>C(N(CC)CC)C>[OH:48][CH:15]([O:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)[CH2:14][C@@H:10]1[CH2:11][CH2:12][CH2:13][N:9]1[C:7]([C@@H:33]1[CH2:32][CH2:31][CH2:27][N:26]1[C:42]([NH:41][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:43])=[O:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 76639Benzyl isocyanateHCID 145742L-ProlineHCID 57133844(S)-1-(tert-Butoxycarbonyl)-2-[1-hydroxy-2-(p-methoxyphenoxy)ethyl]pyrrolidine

Product 1

HCID 86749642(S)-2-[[(S)-2-(Hydroxy-2-(p-methoxyphenoxy)ethyl]-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4N Hydrochloric acid (1,4-dioxane solution, 50 ml) was added to (S)-1-(tert-butoxycarbonyl)-2-[1-hydroxy-2-(p-methoxyphenoxy)ethyl]pyrrolidine (8.03 g), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated and the residue was reacted, in the same manner as in Example 3-a), with N-(benzylaminocarbonyl)-L-proline obtained by stirring L-proline (2.63 g), benzyl isocyanate (2.58 g) and triethylamine (2.31 g) in DMF (25 ml) at room temperature for 1 hour to give the title compound (6.31 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was reacted, in the same manner as in Example 3-a), with N-(benzylaminocarbonyl)-L-proline
  3. customobtained

Sources & evidence

ORD record
ord-ebbdd96556a34845bce43030e5f9e304
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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