1,2-Pyrrolidinedicarboxylic acid, 4-(methoxymethyl)-, 1-(1,1-dimethylethyl) ester, (2S,4S)- → tert-butyl (2S,4S)-2-(9-{2-[(2S,4S)-1-[N-(methoxycarbonyl)-L-valyl]-4-(trifluoromethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl]-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl)-4-(methoxymethyl)pyrrolidine-1-carboxylate

HRID 2172500Notes

Reaction equation

HRID 2172500 reaction equation
COC(N[C@H](C(N1[C@@H](C)CC[C@H]1C1[NH:22][C:21]2[C:23]3[C:28]([CH:29]=[CH:30][C:20]=2[N:19]=1)=[CH:27][C:26]1[C:31]2[C:36]([CH2:37][O:38][C:25]=1[CH:24]=3)=[CH:35][C:34]([C:39]1[NH:43]C([C@@H]3C[C@H](COC)CN3C(OC(C)(C)C)=O)=[N:41][CH:40]=1)=[CH:33][CH:32]=2)=O)C(C)C)=O.[CH3:59][O:60][C:61]([NH:63][C@@H:64]([CH:79]([CH3:81])[CH3:80])[C:65]([N:67]1[CH2:71][C@@H:70]([C:72]([F:75])([F:74])[F:73])[CH2:69][C@H:68]1[C:76](O)=O)=[O:66])=[O:62].[C:82]([O:86][C:87]([N:89]1[CH2:93][C@@H:92]([CH2:94][O:95][CH3:96])[CH2:91][C@H:90]1[C:97](O)=O)=[O:88])([CH3:85])([CH3:84])[CH3:83]>>[CH3:59][O:60][C:61]([NH:63][C@H:64]([C:65]([N:67]1[CH2:71][C@@H:70]([C:72]([F:75])([F:74])[F:73])[CH2:69][C@H:68]1[C:76]1[NH:43][C:39]([C:34]2[CH:35]=[C:36]3[CH2:37][O:38][C:25]4[CH:24]=[C:23]5[C:28]([CH:29]=[CH:30][C:20]6[N:19]=[C:97]([C@@H:90]7[CH2:91][C@H:92]([CH2:94][O:95][CH3:96])[CH2:93][N:89]7[C:87]([O:86][C:82]([CH3:83])([CH3:84])[CH3:85])=[O:88])[NH:22][C:21]=65)=[CH:27][C:26]=4[C:31]3=[CH:32][CH:33]=2)=[CH:40][N:41]=1)=[O:66])[CH:79]([CH3:81])[CH3:80])=[O:62]

Participants

4

Reactant 3

HCID 696720591,2-Pyrrolidinedicarboxylic acid, 4-(methoxymethyl)-, 1-(1,1-dimethylethyl) ester, (2S,4S)-HCID 69673586(2S,4S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-4-(trifluoromethyl)pyrrolidine-2-carboxylic acidHCID 1784956861-Pyrrolidinecarboxylic acid, 2-[5-[1,11-dihydro-2-[(2S,5S)-1-[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-5-methyl-2-pyrrolidinyl][2]benzopyrano[4',3':6,7]naphth[1,2-d]imidazol-9-yl]-1H-imidazol-2-yl]-4-(methoxymethyl)-, 1,1-dimethylethyl ester, (2S,4S)-

Product 1

HCID 178495666tert-butyl (2S,4S)-2-(9-{2-[(2S,4S)-1-[N-(methoxycarbonyl)-L-valyl]-4-(trifluoromethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl]-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl)-4-(methoxymethyl)pyrrolidine-1-carboxylate

Procedure

The title compound was prepared as in example OF for compound tert-butyl (2S,4S)-2-[5-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-valyl]-5-methylpyrrolidin-2-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine-1-carboxylate, by using (2S,4S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-4-(trifluoromethyl)pyrrolidine-2-carboxylic acid in place of (2S,4S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidine-2-carboxylic acid and (2S,4S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidine-2-carboxylic acid in place of (2S,5S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylic acid.

Sources & evidence

ORD record
ord-3ab6dbf25841476582fdc7f681bcc7fd
Source dataset
uspto-grants-2015_06
Patent number
US09051340B2

Reaction notes

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