(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidine → (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(6-allyloxy-3-(E-2-allyloxycarbonyl-1-ethenyl)phenylcarbamoyl)pyrrolidine

HRID 260308Notes

Reaction equation

HRID 260308 reaction equation
[CH2:1]([O:4][C:5]1[CH:18]=[CH:17][C:8]([CH:9]=[CH:10][C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])=[CH:7][C:6]=1[NH2:19])[CH:2]=[CH2:3].[C:20]([S:23][C@@H:24]1[CH2:28][N:27]([C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])[C@H:26]([C:35](O)=[O:36])[CH2:25]1)(=[O:22])[CH3:21].NC1C=C(C=CC=1)C=CC(OCC=C)=O>>[C:20]([S:23][C@@H:24]1[CH2:28][N:27]([C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])[C@H:26]([C:35](=[O:36])[NH:19][C:6]2[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:18][CH:17]=[C:8](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])[CH:7]=2)[CH2:25]1)(=[O:22])[CH3:21]

Participants

4

Reactant 3

HCID 15299255(2S,4S)-4-Acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidineHCID 54090444Allyl 4-allyloxy-3-aminocinnamateHCID 54165426Allyl 3-aminocinnamate

Product 1

HCID 86749573(2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(6-allyloxy-3-(E-2-allyloxycarbonyl-1-ethenyl)phenylcarbamoyl)pyrrolidine

Procedure

Allyl 4-allyloxy-3-aminocinnamate was condensed with (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-carboxypyrrolidine by the method described in example 1 for allyl 3-aminocinnamate to give (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-(6-allyloxy-3-(E-2-allyloxycarbonyl-1-ethenyl)phenylcarbamoyl)pyrrolidine.

Sources & evidence

ORD record
ord-1eea76a397184006aa501dbfecfceb1a
Source dataset
uspto-grants-1996_06
Patent number
US05527791

Reaction notes

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