HCID 70050443, compound → HCID 54483152, compound

HRID 1720489Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:34][CH2:33][CH2:32][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:31])[CH2:21][S@@:22]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[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[CH2:34][CH2:33][CH2:32][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:31])[CH2:21][S@@:22]([C:24]1[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=1)=[O:23])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 70050443HCID 70050443, compound

HCID 86749402Dmso dcc

Product 1

HCID 54483152HCID 54483152, compoundYield 45.6%

Procedure

(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-{1-hydroxy-2-[(S)-p-tolylsulfinyl]ethyl}pyrrolidine (357 mg) was subjected to DMSO-DCC oxidation as in Example 1-D), and the reaction product was purified by medium pressure liquid chromatography (silica gel, eluate; chloroform:methanol=99:1) to give 162 mg of the title compound (See Table 4).

Workup

customwas purified by medium pressure liquid chromatography (silica gel, eluate; chloroform:methanol=99:1)

Sources & evidence

ORD record: ord-3c8cdd9f29b646ae8a8d765f46d04e62
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05506256

Reaction notes

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