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

HRID 1720487Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:33][CH2:32][CH2:31][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:30])[CH2:21][S@@:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[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[CH2:33][CH2:32][CH2:31][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:30])[CH2:21][S@@:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 54163276(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-{1-hydroxy-2-[(S)-phenylsulfinyl]ethyl}pyrrolidine

HCID 86749402Dmso dcc

Product 1

HCID 54001662(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-{[(S)-phenylsulfinyl]acetyl}pyrrolidineYield 40.5%

Procedure

(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-{1-hydroxy-2-[(S)-phenylsulfinyl]ethyl}pyrrolidine (600 mg) was subjected to DMSO-DCC oxidation as in Example 1-D), followed by purification of the reaction product by medium pressure silica gel column chromatography (eluate; chloroform:methanol=99.5: 0.5) to give 242 mg of the title compound (See Table 3 ).

Workup

customfollowed by purification of the reaction product by medium pressure silica gel column chromatography (eluate; chloroform:methanol=99.5: 0.5)

Sources & evidence

ORD record: ord-9486ac57b7af4061be530548ba9a56e8
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05506256

Reaction notes

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