HCID 69675210, compound → (R)-2-((S)-2-(5-(4-(6-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)thiazolidin-3-yl)-2-oxo-1-phenylethylcarbamic acid methyl ester

HRID 1751564Notes

Reaction equation

COC(=O)N[C@@H](C(C)C)C(N1[C@H](C2NC(C3C=CC(C4C=CC5C(=CC=C(C6NC([C@@H]7CCCN7[C:48](=[O:61])[C@H:49]([NH:56][C:57]([O:59][CH3:60])=[O:58])[C:50]7[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=7)=NC=6)C=5)C=4)=CC=3)=CN=2)CC2(OCCO2)C1)=O.Cl.Cl.Cl.Cl.[CH3:70][CH:71]([CH3:116])[C@H:72]([NH:111][C:112](=[O:115])[O:113][CH3:114])[C:73](=[O:110])[N:74]1[CH2:78][CH2:77][CH2:76][C@H:75]1[C:79]1[NH:80][C:81]([C:84]2[CH:93]=[CH:92][C:91]3[C:86](=[CH:87][CH:88]=[C:89]([C:94]4[CH:99]=[CH:98][C:97]([C:100]5[NH:104][C:103]([C@H:105]6[NH:109][CH2:108][CH2:107][S:106]6)=[N:102][CH:101]=5)=[CH:96][CH:95]=4)[CH:90]=3)[CH:85]=2)=[CH:82][N:83]=1>>[CH3:60][O:59][C:57](=[O:58])[NH:56][C@H:49]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:48]([N:109]1[CH2:108][CH2:107][S:106][C@H:105]1[C:103]1[NH:104][C:100]([C:97]2[CH:96]=[CH:95][C:94]([C:89]3[CH:88]=[CH:87][C:86]4[C:91](=[CH:92][CH:93]=[C:84]([C:81]5[NH:80][C:79]([C@@H:75]6[CH2:76][CH2:77][CH2:78][N:74]6[C:73](=[O:110])[C@@H:72]([NH:111][C:112]([O:113][CH3:114])=[O:115])[CH:71]([CH3:116])[CH3:70])=[N:83][CH:82]=5)[CH:85]=4)[CH:90]=3)=[CH:99][CH:98]=2)=[CH:101][N:102]=1)=[O:61]

Participants

Reactant 2

HCID 69675210HCID 69675210, compound

HCID 131733632HCID 131733632, compound

Product 1

HCID 69675730(R)-2-((S)-2-(5-(4-(6-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)thiazolidin-3-yl)-2-oxo-1-phenylethylcarbamic acid methyl ester

Procedure

The title compound was prepared according to the method employed to prepare (S)-1-((S)-8-(5-(4-(6-(2-((S)-1-((R)-2-(methoxycarbonylamino)-2-phenylacetyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-3-methyl-1-oxobutan-2-ylcarbamic acid methyl ester, except that methyl (S)-3-methyl-1-oxo-1-((S)-2-(5-(6-(4-(2-((S)-thiazolidin-2-yl)-1H-imidazol-5-yl)phenyl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate 4HCl salt was used instead of methyl (S)-3-methyl-1-oxo-1-((S)-8-(5-(4-(6-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)butan-2-ylcarbamate 3HCl salt. MS (ESI) m/z 841.83 [M+H]+. (25 mg, 12%).

Sources & evidence

ORD record: ord-ac8245c8cfc7445ea6a5782924a310ae
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156823B2

Reaction notes

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