1,2-Pyrrolidinedicarboxylic acid, 4-(methoxymethyl)-, 1-(1,1-dimethylethyl) ester, (2S,4S)- → Di Boc Velpatasvir

HRID 1751696Notes

Reaction equation

HRID 1751696 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:6]([C:16](OCC(C2C=CC3C4C=C5CCC(Br)C(=O)C5=CC=4OCC=3C=2)=O)=O)[CH2:5]1.COC(N[C@H](C(N1[C@@H](C)CC[C@H]1C1[NH:63][C:62]2[C:64]3[C:69]([CH:70]=[CH:71][C:61]=2[N:60]=1)=[CH:68][C:67]1[C:72]2[C:77]([CH2:78][O:79][C:66]=1[CH:65]=3)=[CH:76][C:75]([C:80]1[NH:84]C([C@@H]3C[C@H](COC)CN3C(OC(C)(C)C)=O)=[N:82][CH:81]=1)=[CH:74][CH:73]=2)=O)C(C)C)=O.[C:100]([O:104][C:105]([N:107]1[CH2:111][C@@H:110]([CH2:112][O:113][CH3:114])[CH2:109][C@H:108]1[C:115](O)=O)=[O:106])([CH3:103])([CH3:102])[CH3:101]>>[C:12]([O:11][C:9]([N:7]1[CH2:8][C@@H:4]([CH2:3][O:2][CH3:1])[CH2:5][C@H:6]1[C:16]1[NH:63][C:62]2[C:64]3[C:69]([CH:70]=[CH:71][C:61]=2[N:60]=1)=[CH:68][C:67]1[C:72]2[C:77]([CH2:78][O:79][C:66]=1[CH:65]=3)=[CH:76][C:75]([C:80]1[NH:84][C:115]([C@@H:108]3[CH2:109][C@H:110]([CH2:112][O:113][CH3:114])[CH2:111][N:107]3[C:105]([O:104][C:100]([CH3:101])([CH3:102])[CH3:103])=[O:106])=[N:82][CH:81]=1)=[CH:74][CH:73]=2)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 3

HCID 696720591,2-Pyrrolidinedicarboxylic acid, 4-(methoxymethyl)-, 1-(1,1-dimethylethyl) ester, (2S,4S)-HCID 69675164(2S,4S)-2-(2-(9-Bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 1-tert-butyl 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylateHCID 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 178495698Di Boc Velpatasvir

Procedure

tert-Butyl (2S,4S)-2-(5-{2-[(2S,4S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidin-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 was prepared from (2S,4S)-2-(2-(9-bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 1-tert-butyl 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate by the same method employed in the synthesis of 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, replacing (2S,5S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carboxylic acid with (2S,4S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidine-2-carboxylic acid.

Sources & evidence

ORD record
ord-63f1a3f753ab43278474ddcaaddaa3c7
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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