(S)-2-tert-Butyl 3-methyl 7-((S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2,5-dihydro-1H-pyrrol-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate → (S)-2-tert-Butyl 3-methyl 7-((3R,5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidin-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate

HRID 339282Notes

Reaction equation

HRID 339282 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(N[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:71]([O:75][C:76]([N:78]1[C@H:82]([C:83]([O:85][CH3:86])=[O:84])[CH:81]=[C:80]([C:87]2[CH:96]=[C:95]3[C:90]([CH2:91][C@@H:92]([C:104]([O:106][CH3:107])=[O:105])[N:93]([C:97]([O:99][C:100]([CH3:103])([CH3:102])[CH3:101])=[O:98])[CH2:94]3)=[CH:89][CH:88]=2)[CH2:79]1)=[O:77])([CH3:74])([CH3:73])[CH3:72]>>[C:71]([O:75][C:76]([N:78]1[C@H:82]([C:83]([O:85][CH3:86])=[O:84])[CH2:81][C@H:80]([C:87]2[CH:96]=[C:95]3[C:90]([CH2:91][C@@H:92]([C:104]([O:106][CH3:107])=[O:105])[N:93]([C:97]([O:99][C:100]([CH3:102])([CH3:101])[CH3:103])=[O:98])[CH2:94]3)=[CH:89][CH:88]=2)[CH2:79]1)=[O:77])([CH3:74])([CH3:72])[CH3:73]

Participants

3

Reactant 2

HCID 86705924(S)-2-tert-Butyl 3-methyl 7-((S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2,5-dihydro-1H-pyrrol-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylateHCID 117710478(3S)-2-[(2S)-3,3-dimethyl-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]-7-[[(3S,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]amino]-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-3,4-dihydro-1H-isoquinoline-3-carboxamide

Product 1

HCID 126517029(S)-2-tert-Butyl 3-methyl 7-((3R,5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidin-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylateYield 88.5%

Procedure

Following a procedure analogous to that for the synthesis of Compound C of Example 20, (S)-2-tert-butyl 3-methyl 7-((5)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-2,5-dihydro-1H-pyrrol-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate (563 mg, 1.09 mmol) was converted to the title compound (500 mg, 88%). MS (ESI) m/z 519.5 (M+H)+.

Sources & evidence

ORD record
ord-2aa2b92beac440aca82444b5dc11e4ad
Source dataset
uspto-grants-2014_11
Patent number
US08889712B2

Reaction notes

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