(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2(isopropylsulfinyl)ethyl]pyrrolidine → (2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[(isopropylsulfinyl)-acetyl]pyrrolidine

HRID 1720486Notes

Reaction equation

HRID 1720486 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:30][CH2:29][CH2:28][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:27])[CH2:21][S:22]([CH:24]([CH3:26])[CH3:25])=[O:23])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.C1CCC(N=C=NC2CCCCC2)CC1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:30][CH2:29][CH2:28][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:27])[CH2:21][S:22]([CH:24]([CH3:25])[CH3:26])=[O:23])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 57234092(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2(isopropylsulfinyl)ethyl]pyrrolidineHCID 86749402Dmso dcc

Product 1

HCID 57250007(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[(isopropylsulfinyl)-acetyl]pyrrolidineYield 37.6%

Procedure

(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[1-hydroxy-2(isopropylsulfinyl)ethyl]pyrrolidine (1.34 g) was subjected to DMSO-DCC oxidation as in Example 1-D) to give 502 mg of the title compound (See Table 3).

Sources & evidence

ORD record
ord-7d5c42c769144d09b0a4094db0fd5e35
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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