L-Proline, 1-(1-oxo-3-phenylpropyl)- → (2S)-2-{2-[4-(Benzyloxy)phenoxy]-1-hydroxyethyl}-1-[N-(3-phenylpropionyl)-L-prolyl]pyrrolidine

HRID 1720509Notes

Reaction equation

HRID 1720509 reaction equation
[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:12]([O:13][CH2:14][CH:15]([C@@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22](OC(C)(C)C)=[O:23])[OH:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31]1([CH2:37][CH2:38][C:39]([N:41]2[CH2:48][CH2:47][CH2:46][C@H:42]2C(O)=O)=[O:40])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:12]([O:13][CH2:14][CH:15]([C@@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22](=[O:23])[C@@H:48]2[CH2:47][CH2:46][CH2:42][N:41]2[C:39](=[O:40])[CH2:38][CH2:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[OH:16])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10354601L-Proline, 1-(1-oxo-3-phenylpropyl)-HCID 57047086(2S)-2-{2-[4-(Benzyloxy)phenoxy]-1-hydroxyethyl}-1-(tert-butoxycarbonyl)pyrrolidine

Product 1

HCID 67771548(2S)-2-{2-[4-(Benzyloxy)phenoxy]-1-hydroxyethyl}-1-[N-(3-phenylpropionyl)-L-prolyl]pyrrolidineYield 81.1%

Procedure

By the same procedure as in Example 26-D), while using (2S)-2-{2-[4-(benzyloxy)phenoxy]-1-hydroxyethyl}-1-(tert-butoxycarbonyl)pyrrolidine (1.71 g) and N-(3-phenylpropionyl)- L-proline (1.10 g), there was obtained 1.82 g of the title compound.

Sources & evidence

ORD record
ord-6c8a73a5ff1d4967aece35dc15966474
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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