N-Methoxycarbonyl-2-phenylglycine → Methyl (S)-1-((S)-2-(5-(4'-(2-((1R,3S,4S)-2-((S)-2-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2-azabicyclo[2.2.1]heptan-3-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

HRID 1751479Notes

Reaction equation

HRID 1751479 reaction equation
[CH3:1][O:2][C:3](=[O:66])[NH:4][CH:5](C1C=CC=CC=1)[C:6]([N:8]1[CH2:12][C:11](F)(F)[CH2:10][CH:9]1[C:15]1[NH:16][C:17]([C:20]2[CH:25]=[CH:24][C:23](C3C=CC4C(=CC=C(C5NC(C6CCCN6C(=O)C(NC(OC)=O)C6CCOCC6)=NC=5)C=4)C=3)=[CH:22][CH:21]=2)=[CH:18][N:19]=1)=[O:7].BrC1C=[C:70]2[C:75](=CC=1)[CH:74]=[C:73]([C:78]1[NH:82][C:81]([C@@H:83]3[CH2:87][CH2:86][CH2:85][N:84]3[C:88]([O:90]CC3C=CC=CC=3)=O)=[N:80][CH:79]=1)[CH:72]=[CH:71]2.[C:98]([O:102][C:103]([N:105]1[CH:110](C(O)=O)[CH:109]2[CH2:114]C1C[CH2:108]2)=[O:104])(C)(C)C.C(OC(N1[CH2:126][C:125](F)(F)[CH2:124][CH:123]1[C:129]([OH:131])=O)=O)(C)(C)C.COC(N[CH:137](C1CCOCC1)[C:138](O)=O)=O.COC(NC(C1C=CC=CC=1)C(O)=O)=O>>[CH3:1][O:2][C:3]([NH:4][C@@H:5]([CH:124]1[CH2:123][CH2:129][O:131][CH2:126][CH2:125]1)[C:6]([N:8]1[C@H:9]([C:15]2[NH:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:70]4[CH:71]=[CH:72][C:73]([C:78]5[NH:82][C:81]([C@@H:83]6[CH2:87][CH2:86][CH2:85][N:84]6[C:88](=[O:90])[C@@H:110]([NH:105][C:103](=[O:104])[O:102][CH3:98])[CH:109]([CH3:108])[CH3:114])=[N:80][CH:79]=5)=[CH:74][CH:75]=4)=[CH:22][CH:21]=3)=[CH:18][N:19]=2)[C@@H:10]2[CH2:138][C@H:137]1[CH2:12][CH2:11]2)=[O:7])=[O:66]

Participants

7

Reactant 6

HCID 596264N-Methoxycarbonyl-2-phenylglycineHCID 150563882-(tert-Butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acidHCID 235125141-((Tert-butoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acidHCID 585162412-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acidHCID 70653414(S)-benzyl 2-(5-(2-bromonaphthalen-6-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylateHCID 86708747HCID 86708747, compound

Product 1

HCID 86708751Methyl (S)-1-((S)-2-(5-(4'-(2-((1R,3S,4S)-2-((S)-2-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetyl)-2-azabicyclo[2.2.1]heptan-3-yl)-1H-imidazol-5-yl)biphenyl-4-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Procedure

The title compound was prepared as described for {2-[4,4-Difluoro-2-(5-{4-[6-(2-{1-[2-methoxycarbonylamino-2-(tetrahydro-pyran-4-yl)-acetyl]-pyrrolidin-2-yl}-3H-imidazol-4-yl)-naphthalen-2-yl]-phenyl}-1H-imidazol-2-yl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid methyl ester, substituting (S)-benzyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate for (S)-benzyl 2-(5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate, 2-Azabicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester for 4,4-Difluoro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester, and Methoxycarbonylamino-(tetrahydro-pyran-4-yl)-acetic acid for Methoxycarbonylamino-phenyl-acetic acid. LCMS-ESI+: calculated for C44H55N8O7: 807.4; observed [M+1]+: 807.4.

Sources & evidence

ORD record
ord-82c078b321704c85b165ad1fa801bba0
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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