(S)-(-)-4-methoxyphenyl methyl sulfoxide → (2S)-1-(N-Benzylaminocarbonyl-L-prolyl)-2-{[(S)-4-methoxyphenylsulfinyl]acetyl}pyrrolidine

HRID 1720501Notes

Reaction equation

HRID 1720501 reaction equation
C(O[C:9](=[O:32])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:31])[C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])C1C=CC=CC=1.[CH3:33][S@@:34]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)=[O:35]>>[CH2:24]([NH:23][C:21]([N:17]1[CH2:18][CH2:19][CH2:20][C@H:16]1[C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9](=[O:32])[CH2:33][S@@:34]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)=[O:35])=[O:31])=[O:22])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 12072511(S)-(-)-4-methoxyphenyl methyl sulfoxideHCID 54203628N-Benzylaminocarbonyl-L-prolyl-L-proline benzyl ester

Product 1

HCID 53731509(2S)-1-(N-Benzylaminocarbonyl-L-prolyl)-2-{[(S)-4-methoxyphenylsulfinyl]acetyl}pyrrolidineYield 27.6%

Procedure

By the same procedure as in Example 15-D) using N-benzylaminocarbonyl-L-prolyl-L-proline benzyl ester (2.00 g) and (S)-(-)-4-methoxyphenyl methyl sulfoxide (780 mg) as obtained in Example 15-C), there was obtained 629 mg of the title compound as colorless needles (See Table 7).

Workup

  1. customas obtained in Example 15-C), there

Sources & evidence

ORD record
ord-bbf5c93b052c4134bc0b9397633af16b
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

Loading…