2-Aminophenol → (2R,4R)-4-(Aminomethyl)-N-[(5-phenyl-2-benzimidazolyl)methyl]-2-pyrrolidinecarboxamide

HRID 2185515Notes

Reaction equation

HRID 2185515 reaction equation
C(OC([NH:11][CH2:12][C:13](O)=O)=O)C1C=CC=CC=1.NC1C=CC=CC=1O.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:27][C:26]=1[NH2:37].C(OC(NCC(N[C@H]1CN(C(OC(C)(C)C)=O)[C@H](C(O)=O)C1)=O)=O)(C)(C)C.C(OC([NH:72][CH2:73][C@@H:74]1[CH2:78][N:77](C(OC(C)(C)C)=O)[C@@H:76]([C:86]([OH:88])=O)[CH2:75]1)=O)(C)(C)C>>[NH2:72][CH2:73][C@@H:74]1[CH2:78][NH:77][C@@H:76]([C:86]([NH:11][CH2:12][C:13]2[NH:37][C:26]3[CH:27]=[C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:29]=[CH:30][C:25]=3[N:24]=2)=[O:88])[CH2:75]1

Participants

6

Reactant 5

HCID 58012-AminophenolHCID 14349BenzyloxycarbonylglycineHCID 6452000(1,1'-Biphenyl)-3,4-diamineHCID 21341559trans-4-(N-tert-butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-prolineHCID 53725027trans-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-D-proline

Product 1

HCID 57001021(2R,4R)-4-(Aminomethyl)-N-[(5-phenyl-2-benzimidazolyl)methyl]-2-pyrrolidinecarboxamide

Procedure

This compound was prepared as in Compound M77, replacing N-(Benzyloxycarbonyl)-D-homophenylalanine with N-(Benzyloxycarbonyl)glycine, 2-aminophenol with 1,2-diamino-4-phenylbenzene and trans-4-(N-tert-butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-proline with trans-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-D-proline.

Sources & evidence

ORD record
ord-e3f9ddaf0aae4295b780f88433e8f81b
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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