(S)-2-((S)-2-((S)-2-((tert-Butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid → (S)-2-(tert-Butoxycarbonyl)-7-((3R,5S)-1-(tert-butoxycarbonyl)-5-carboxypyrrolidin-3-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 339283Notes

Reaction equation

C(OC(N(C)[C@@H](C)C(N[C@@H](C(C)(C)C)C(N1[C@H](C(=O)N[C@H]2C3C(=CC=CC=3)CCC2)CC2C(=CC(C(O)=O)=CC=2)C1)=O)=O)=O)(C)(C)C.[C:48]([O:52][C:53]([N:55]1[C@H:59]([C:60]([O:62]C)=[O:61])[CH2:58][CH:57]([C:64]2[CH:73]=[C:72]3[C:67]([CH2:68][C@@H:69]([C:81]([O:83]C)=[O:82])[N:70]([C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[CH2:71]3)=[CH:66][CH:65]=2)[CH2:56]1)=[O:54])([CH3:51])([CH3:50])[CH3:49]>>[C:77]([O:76][C:74]([N:70]1[C@H:69]([C:81]([OH:83])=[O:82])[CH2:68][C:67]2[C:72](=[CH:73][C:64]([C@H:57]3[CH2:58][C@@H:59]([C:60]([OH:62])=[O:61])[N:55]([C:53]([O:52][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:54])[CH2:56]3)=[CH:65][CH:66]=2)[CH2:71]1)=[O:75])([CH3:80])([CH3:79])[CH3:78]

Participants

Reactant 2

HCID 86705870(S)-2-((S)-2-((S)-2-((tert-Butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid

HCID 86705926(3S)-2-tert-butyl 3-methyl 7-((5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidin-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate

Product 1

HCID 86705925(S)-2-(tert-Butoxycarbonyl)-7-((3R,5S)-1-(tert-butoxycarbonyl)-5-carboxypyrrolidin-3-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidYield 95.6%

Procedure

Following a procedure analogous to that for the synthesis of Compound K of Example 1, (3S)-2-tert-butyl 3-methyl 7-((5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidin-3-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate (500 mg, 0.96 mmol) was converted to the title compound (450 mg, 95%). MS (ESI+) m/z 491.4 (M+H)+.

Sources & evidence

ORD record: ord-d249bc8502144ff8944008bf26332880
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889712B2

Reaction notes

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