HCID 57230620, compound → HCID 57059660, compound

HRID 1720497Notes

Reaction equation

HRID 1720497 reaction equation
[CH2:1]([NH:8][C:9]([N:11]1[CH2:32][CH2:31][CH2:30][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:29])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[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]([NH:8][C:9]([N:11]1[CH2:32][CH2:31][CH2:30][C@H:12]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:29])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 57230620HCID 57230620, compoundHCID 86749402Dmso dcc

Product 1

HCID 57059660HCID 57059660, compoundYield 53.8%

Procedure

(2S)-1-(N-Benzylaminocarbonyl-L-prolyl)-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine (798 mg) was subjected to DMSO-DCC oxidation as in Example 1D), followed by recrystallization from ethyl acetate-hexane to give 427 mg of the title compound (See Table 6).

Workup

  1. customfollowed by recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ea02a28b7d764a5ba1be6732bf751c5b
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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