(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 → (2S,4S)-1-(tert-Butoxycarbonyl)-4-(((S)-2-(tert-butoxycarbonyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)oxy)pyrrolidine-2-carboxylic acid

HRID 339245Notes

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:64]([C:65](=[O:77])[NH:66][C@H:67]2[C:76]3[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=3)[CH2:70][CH2:69][CH2:68]2)[CH2:63][C:62]2[C:57](=[CH:58][C:59]([O:78][C@@H:79]3[CH2:83][N:82]([C:84]([O:86][C:87]([CH3:90])([CH3:89])[CH3:88])=[O:85])[C@H:81]([C:91]([O:93]C)=[O:92])[CH2:80]3)=[CH:60][CH:61]=2)[CH2:56]1)=[O:54])([CH3:51])([CH3:50])[CH3:49]>>[C:87]([O:86][C:84]([N:82]1[CH2:83][C@@H:79]([O:78][C:59]2[CH:58]=[C:57]3[C:62]([CH2:63][C@@H:64]([C:65](=[O:77])[NH:66][C@H:67]4[C:76]5[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=5)[CH2:70][CH2:69][CH2:68]4)[N:55]([C:53]([O:52][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:54])[CH2:56]3)=[CH:61][CH:60]=2)[CH2:80][C@H:81]1[C:91]([OH:93])=[O:92])=[O:85])([CH3:88])([CH3:89])[CH3:90]

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 86705879(2S,4S)-1-tert-Butyl 2-methyl 4-(((S)-2-(tert-butoxycarbonyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)oxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 86705880(2S,4S)-1-(tert-Butoxycarbonyl)-4-(((S)-2-(tert-butoxycarbonyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)oxy)pyrrolidine-2-carboxylic acidYield 96%

Procedure

Following a procedure analogous to that for the synthesis of Compound K of Example 1, (2S,4S)-1-tert-butyl 2-methyl 4-(((S)-2-(tert-butoxycarbonyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)oxy)pyrrolidine-1,2-dicarboxylate (66 mg, 0.10 mmol) was converted to the title compound (61 mg, 94%). MS (ESI+) m/z 636.3 (M+H)+.

Sources & evidence

ORD record: ord-004ce7d6d7c94e4186cf3b11527a1193
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889712B2

Reaction notes

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