(3S)-2-[(2S)-3,3-dimethyl-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]-7-[(3R,5S)-1-[(2S)-3,3-dimethyl-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]-5-[[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]carbamoyl]pyrrolidin-3-yl]-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-3,4-dihydro-1H-isoquinoline-3-carboxamide → (S)-2-tert-butyl 3-methyl 7-((3R,5S)-1-(tert-butoxycarbonyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate

HRID 339263Notes

Reaction equation

CC(C)(C)[C@H](NC(=O)[C@@H](NC)C)C(N1[C@H](C(N[C@H]2C3C(=CC=CC=3)CCC2)=O)CC2C(=CC([C@H]3C[C@@H](C(=O)N[C@H]4C5C(=CC=CC=5)CCC4)N(C(=O)[C@@H](NC(=O)[C@@H](NC)C)C(C)(C)C)C3)=CC=2)C1)=O.[C:70]([O:74][C:75]([N:77]1[C@H:81]([C:82](=[O:94])[NH:83][C@H:84]2[C:93]3[C:88](=[CH:89][CH:90]=[CH:91][CH:92]=3)[CH2:87][CH2:86][CH2:85]2)[CH:80]=[C:79]([C:95]2[CH:104]=[C:103]3[C:98]([CH2:99][C@@H:100]([C:112]([O:114][CH3:115])=[O:113])[N:101]([C:105]([O:107][C:108]([CH3:111])([CH3:110])[CH3:109])=[O:106])[CH2:102]3)=[CH:97][CH:96]=2)[CH2:78]1)=[O:76])([CH3:73])([CH3:72])[CH3:71]>>[C:70]([O:74][C:75]([N:77]1[C@H:81]([C:82](=[O:94])[NH:83][C@H:84]2[C:93]3[C:88](=[CH:89][CH:90]=[CH:91][CH:92]=3)[CH2:87][CH2:86][CH2:85]2)[CH2:80][C@H:79]([C:95]2[CH:104]=[C:103]3[C:98]([CH2:99][C@@H:100]([C:112]([O:114][CH3:115])=[O:113])[N:101]([C:105]([O:107][C:108]([CH3:110])([CH3:109])[CH3:111])=[O:106])[CH2:102]3)=[CH:97][CH:96]=2)[CH2:78]1)=[O:76])([CH3:73])([CH3:71])[CH3:72]

Participants

Reactant 2

HCID 72704974(3S)-2-[(2S)-3,3-dimethyl-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]-7-[(3R,5S)-1-[(2S)-3,3-dimethyl-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]-5-[[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]carbamoyl]pyrrolidin-3-yl]-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-3,4-dihydro-1H-isoquinoline-3-carboxamide

HCID 86705902(S)-2-tert-Butyl 3-methyl 7-((S)-1-(tert-butoxycarbonyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-2,5-dihydro-1H-pyrrol-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate

Product 1

HCID 86705905(S)-2-tert-butyl 3-methyl 7-((3R,5S)-1-(tert-butoxycarbonyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylateYield 89%

Procedure

Following a procedure analogous to that for the synthesis of Compound E of Example 22, (S)-2-tert-butyl 3-methyl 7-((S)-1-(tert-butoxycarbonyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-2,5-dihydro-1H-pyrrol-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate (730 mg, 1.16 mmol) was converted to the title compound (650 mg, 89%). MS (ESI+) m/z 634.5 (M+H)+.

Sources & evidence

ORD record: ord-7e8bd836133545eabb2515a2d0a49b3e
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889712B2

Reaction notes

Loading…