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

HRID 1720502Notes

Reaction equation

HRID 1720502 reaction equation
C([O:8][C:9](=O)[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:33])[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][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)=[O:22])C1C=CC=CC=1.[CH3:35][S@@:36]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)=[O:37]>>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][NH:23][C:21]([N:17]2[CH2:18][CH2:19][CH2:20][C@H:16]2[C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:10]2[C:9](=[O:8])[CH2:35][S@@:36]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)=[O:37])=[O:33])=[O:22])=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 12072511(S)-(-)-4-methoxyphenyl methyl sulfoxideHCID 54101220N-(4-methoxybenzylaminocarbonyl)-L-prolyl-L-proline benzyl ester

Product 1

HCID 53744324(2S)-1-[N-(4-Methoxybenzylaminocarbonyl)-L-prolyl]-2-{[(S)-4-methoxyphenylsulfinyl]acetyl}pyrrolidineYield 31.2%

Procedure

By the same procedure as in Example 15-D) using N-(4-methoxybenzylaminocarbonyl)-L-prolyl-L-proline benzyl ester (1.30 g) and (S)-(-)-4-methoxyphenyl methyl sulfoxide (480 mg) as obtained in Example 15-C), there was obtained 460 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-1f27fe0b2a204847a7468781a8397036
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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