p-Chlorothiophenol → (2s,4r)-4-(2-Aminoacetamido)-n-[(1r)-3-methyl-1-[(4-chlorphenylthio)methyl]butyl]-2-pyrrolidinecarboxamide

HRID 2185501Notes

Reaction equation

HRID 2185501 reaction equation
C(O[C:6]([NH:8][C@@H:9]([C:14](O)=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])(C)(C)C.OC1C=CC2C(=CC=CC=2)N=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([SH:35])=[CH:31][CH:30]=1.C(OC(NC[C@@H]1CN(C(OC(C)(C)C)=O)[C@@H](C(O)=O)C1)=O)(C)(C)C.C(OC([NH:67][CH2:68][C:69]([NH:71][C@H:72]1[CH2:76][N:75](C(OC(C)(C)C)=O)[C@H:74](C(O)=O)[CH2:73]1)=[O:70])=O)(C)(C)C>>[NH2:67][CH2:68][C:69]([NH:71][C@H:72]1[CH2:76][NH:75][C@H:74]([C:6]([NH:8][C@@H:9]([CH2:14][S:35][C:32]2[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=2)[CH2:10][CH:11]([CH3:12])[CH3:13])=[O:7])[CH2:73]1)=[O:70]

Participants

6

Reactant 5

HCID 7815p-ChlorothiophenolHCID 637604tert-Butoxycarbonyl-D-leucineHCID 21341559trans-4-(N-tert-butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-prolineHCID 53725027trans-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-D-prolineHCID 178515546HCID 178515546, compound

Product 1

HCID 57072991(2s,4r)-4-(2-Aminoacetamido)-n-[(1r)-3-methyl-1-[(4-chlorphenylthio)methyl]butyl]-2-pyrrolidinecarboxamide

Procedure

This corpound was prepared as for Compound M48, replacing N-tert-butoxycarbonyl-D-homophenylalaine with N-tert-butoxycarbonyl-D-leucine, 2-hydroxyquinoline with 4-chlorothiophenol and trans-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-D-proline with trans-4-(N-tert-butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-proline.

Sources & evidence

ORD record
ord-6bc56d751e104077a6127efe68938c59
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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