2-Ethoxy-1-((2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1H-benzimidazole-7-carboxylic acid → (1R)-1-({[(1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentyl]carbonyl}oxy)ethyl N-pentanoyl-N-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-L-valinate

HRID 2067147Notes

Reaction equation

HRID 2067147 reaction equation
C(OC1N(CC2C=CC(C3C=CC=CC=3C3N(C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)N=NN=3)=CC=2)C2C(C(O)=O)=CC=CC=2N=1)C.[C:53]([N:59]([CH2:67][C:68]1[CH:73]=[CH:72][C:71]([C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][C:75]=2[C:80]2[N:84](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:83]=[N:82][N:81]=2)=[CH:70][CH:69]=1)[C@H:60]([C:64]([OH:66])=[O:65])[CH:61]([CH3:63])[CH3:62])(=[O:58])[CH2:54][CH2:55][CH2:56][CH3:57].[CH3:104][O:105][C@@H:106]1[C@@H:110]([O:111][N+:112]([O-:114])=[O:113])[CH2:109][C@H:108]([C:115]([O:117][CH:118](Cl)[CH3:119])=[O:116])[CH2:107]1.CO[C@@H]1[C@@H](O[N+]([O-])=O)C[C@H](C(O[C@@H](Cl)C)=O)C1>>[C:53]([N:59]([CH2:67][C:68]1[CH:73]=[CH:72][C:71]([C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][C:75]=2[C:80]2[NH:84][N:83]=[N:82][N:81]=2)=[CH:70][CH:69]=1)[C@H:60]([C:64]([O:66][C@@H:118]([O:117][C:115]([C@H:108]1[CH2:109][C@H:110]([O:111][N+:112]([O-:114])=[O:113])[C@@H:106]([O:105][CH3:104])[CH2:107]1)=[O:116])[CH3:119])=[O:65])[CH:61]([CH3:63])[CH3:62])(=[O:58])[CH2:54][CH2:55][CH2:56][CH3:57]

Participants

5

Reactant 4

HCID 103125632-Ethoxy-1-((2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1H-benzimidazole-7-carboxylic acidHCID 23653943(2S)-3-methyl-2-[pentanoyl-[[4-[2-(1-trityltetrazol-5-yl)phenyl]phenyl]methyl]amino]butanoic acidHCID 593640921-chloroethyl (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylate2×HCID 86642385(1S)-1-chloroethyl (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylate2×

Product 1

HCID 178447307(1R)-1-({[(1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentyl]carbonyl}oxy)ethyl N-pentanoyl-N-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-L-valinate

Procedure

The title compound was prepared by following the procedure for example 2, except that the reagent 2-ethoxy-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylic acid was replaced by N-pentanoyl-N-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-L-valine and 1-chloroethyl (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylate (intermediate 2) was replaced by (1S)-1-chloroethyl (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylate (intermediate 3). LC-MS: m/z 667.3 (M+H).

Sources & evidence

ORD record
ord-96bdba94e7a04492ae0f5fa45771556b
Source dataset
uspto-grants-2012_10
Patent number
US08293777B2

Reaction notes

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