1-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid → [1-(2-{5-[6-(4-{2-[1-(2-Dimethylamino-2-phenyl-acetyl)-4-ethoxy-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

HRID 1751478Notes

Reaction equation

HRID 1751478 reaction equation
[CH3:1][O:2][C:3](=[O:62])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:17][C:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:31]4[CH:36]=[CH:35][C:34]([C:37]5[NH:38][C:39]([CH:42]6[CH2:46][CH2:45][CH2:44][N:43]6C(=O)C(NC(OC)=O)(C6C=CC=CC=6)C)=[N:40][CH:41]=5)=[CH:33][CH:32]=4)[CH:27]=3)[CH:22]=2)=[CH:19][N:20]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].[C:63]([O:67]C(N1CCCC1C(O)=O)=O)(C)(C)[CH3:64].[CH3:78][N:79]([CH:81]([C:85]1[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=1)[C:82]([OH:84])=O)[CH3:80].COC(NC(C1C=CC=CC=1)(C)C(O)=O)=O>>[CH3:1][O:2][C:3](=[O:62])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:17][C:18]([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:31]4[CH:32]=[CH:33][C:34]([C:37]5[NH:38][C:39]([CH:42]6[CH2:46][CH:45]([O:67][CH2:63][CH3:64])[CH2:44][N:43]6[C:82](=[O:84])[CH:81]([N:79]([CH3:78])[CH3:80])[C:85]6[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=6)=[N:40][CH:41]=5)=[CH:35][CH:36]=4)[CH:27]=3)[CH:22]=2)=[CH:19][N:20]=1)=[O:10])[CH:6]([CH3:7])[CH3:8]

Participants

5

Reactant 4

HCID 2684721-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 3155992-(Dimethylamino)-2-phenylacetic acidHCID 624897412-Methoxycarbonylamino-2-phenyl-propionic acidHCID 69673751[1-(2-{5-[6-(4-{2-[1-(2-Methoxycarbonylamino-2-phenyl-propionyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

Product 1

HCID 86708750[1-(2-{5-[6-(4-{2-[1-(2-Dimethylamino-2-phenyl-acetyl)-4-ethoxy-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

Procedure

[1-(2-{5-[6-(4-{2-[1-(2-Dimethylamino-2-phenyl-acetyl)-4-ethoxy-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester was prepared following the procedure for [1-(2-{5-[6-(4-{2-[1-(2-Methoxycarbonylamino-2-phenyl-propionyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester, substituting 4-Ethoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester for Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester and Dimethylamino-phenyl-acetic acid for 2-Methoxycarbonylamino-2-phenyl-propionic acid. LCMS-ESI+: calc'd for C49H56N8O5: 836.44 (M+); Found: 837.80 (M+H+).

Sources & evidence

ORD record
ord-5698f599125c4dbbb940c532d226cffa
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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