Hydrochloric Acid → (2S)-2-(1-Hydroxy-2-phenoxyethyl)-1-{N-[3-phenyl-2(S)-(1-piperidinyl)propionyl]-L-prolyl}pyrrolidine

HRID 1720540Notes

Reaction equation

HRID 1720540 reaction equation
Cl.C(O[C:7]([N:9]1[CH2:30][CH2:29][CH2:28][C@H:10]1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][C@H:14]1[CH:18]([OH:27])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:12])=[O:8])(C)(C)C.Cl.[C:32]1([CH2:38][C@H:39]([N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)C(O)=O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[OH:27][CH:18]([C@@H:14]1[CH2:15][CH2:16][CH2:17][N:13]1[C:11](=[O:12])[C@@H:10]1[CH2:28][CH2:29][CH2:30][N:9]1[C:7](=[O:8])[C@@H:39]([N:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1)[CH2:38][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 67771413(2S)-3-phenyl-2-(1-piperidinyl)propionic acid hydrochlorideHCID 70050944(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine

Product 1

HCID 22860067(2S)-2-(1-Hydroxy-2-phenoxyethyl)-1-{N-[3-phenyl-2(S)-(1-piperidinyl)propionyl]-L-prolyl}pyrrolidineYield 84.9%

Procedure

The residue obtained by treating, with 4N hydrochloric acid, (2S)-1-[N-(tert-butoxycarbonyl)-L-prolyl]-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine (751 mg) prepared in Example 46-C) was subjected to condensation with (2S)-3-phenyl-2-(1-piperidinyl)propionic acid hydrochloride (500 mg) in the same manner as in Example 48-B) to give 818 mg of the title compound.

Workup

  1. customThe residue obtained

Sources & evidence

ORD record
ord-52e902c1fd9d44bca6d0f1dca0759a43
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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