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

HRID 2185513Notes

Reaction equation

HRID 2185513 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]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][C:26]=1[NH2:38].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:73][CH2:74][C@H:75]1[CH2:79][N:78](C(OC(C)(C)C)=O)[C@@H:77]([C:87]([OH:89])=O)[CH2:76]1)=O)(C)(C)C>>[NH2:73][CH2:74][C@H:75]1[CH2:79][NH:78][C@@H:77]([C:87]([NH:11][CH2:12][C:13]2[NH:38][C:26]3[CH:27]=[C:28]([CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:29]=[CH:30][C:25]=3[N:24]=2)=[O:89])[CH2:76]1

Participants

6

Reactant 5

HCID 58012-AminophenolHCID 14349BenzyloxycarbonylglycineHCID 21341559trans-4-(N-tert-butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-prolineHCID 218224164-Benzylbenzene-1,2-diamineHCID 53725028cis-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-D-proline

Product 1

HCID 57093598(2R,4S)-4-(Aminomethyl)-N-[(5-benzyl-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 1,2diamino-4-benzylbenzene and trans-4-(N-tert-butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-proline with cis-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-D-proline.

Sources & evidence

ORD record
ord-d6b29a7123c54aed910a855a96542ea2
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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