(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-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 339264Notes

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:72])[NH:61][C@H:62]2[C:71]3[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=3)[CH2:65][CH2:64][CH2:63]2)[CH2:58][C@H:57]([C:73]2[CH:82]=[C:81]3[C:76]([CH2:77][C@@H:78]([C:90]([O:92]C)=[O:91])[N:79]([C:83]([O:85][C:86]([CH3:89])([CH3:88])[CH3:87])=[O:84])[CH2:80]3)=[CH:75][CH:74]=2)[CH2:56]1)=[O:54])([CH3:51])([CH3:50])[CH3:49]>>[C:86]([O:85][C:83]([N:79]1[C@H:78]([C:90]([OH:92])=[O:91])[CH2:77][C:76]2[C:81](=[CH:82][C:73]([C@H:57]3[CH2:58][C@@H:59]([C:60](=[O:72])[NH:61][C@H:62]4[C:71]5[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=5)[CH2:65][CH2:64][CH2:63]4)[N:55]([C:53]([O:52][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:54])[CH2:56]3)=[CH:74][CH:75]=2)[CH2:80]1)=[O:84])([CH3:89])([CH3:88])[CH3:87]

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 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)-dicarboxylate

Product 1

HCID 86705904(S)-2-(tert-Butoxycarbonyl)-7-((3R,5S)-1-(tert-butoxycarbonyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidYield 94%

Procedure

Following a procedure analogous to that for the synthesis of Compound K of Example 1, (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 (650 mg, 1.03 mmol) was converted to the title compound (599 mg, 94%). MS (ESI+) m/z 620.5 (M+H)+.

Sources & evidence

ORD record: ord-cb45a96eb198414ca67a5f4ae3bb32c0
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889712B2

Reaction notes

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