(R)-8-(2-amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one → (R)-6-((3-((4'-(4-((2-((tert-butyldimethylsilyl)oxy)-2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)amino)butyl)-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

HRID 1944958Notes

Reaction equation

[Si](O[C@H](C1C=CC(O)=C2C=1C=CC(=O)N2)CNCCCCCCCCNC(C1C=C(S(C2C=C3C(=C(C)C=2)N=CC(C(N)=O)=C3NC2C=CC=C(OC)C=2)(=O)=O)C=CC=1)=O)(C(C)(C)C)(C)C.[NH2:67][CH2:68][C@@H:69]([C:78]1[C:83]2[O:84][CH2:85][C:86](=[O:88])[NH:87][C:82]=2[C:81]([OH:89])=[CH:80][CH:79]=1)[O:70][Si:71]([C:74]([CH3:77])([CH3:76])[CH3:75])([CH3:73])[CH3:72].[CH3:90][O:91][C:92]1[CH:93]=[C:94]([NH:98][C:99]2[C:108]3[C:103](=[C:104]([CH3:138])[CH:105]=[C:106]([S:109]([C:112]4[CH:117]=[CH:116][CH:115]=[C:114]([C:118](=[O:137])[NH:119][C:120]5[CH:125]=[CH:124][C:123]([C:126]6[CH:131]=[CH:130][C:129]([CH2:132][CH2:133][CH2:134][CH:135]=O)=[CH:128][CH:127]=6)=[CH:122][CH:121]=5)[CH:113]=4)(=[O:111])=[O:110])[CH:107]=3)[N:102]=[CH:101][C:100]=2[C:139]([NH2:141])=[O:140])[CH:95]=[CH:96][CH:97]=1>>[Si:71]([O:70][C@H:69]([C:78]1[C:83]2[O:84][CH2:85][C:86](=[O:88])[NH:87][C:82]=2[C:81]([OH:89])=[CH:80][CH:79]=1)[CH2:68][NH:67][CH2:135][CH2:134][CH2:133][CH2:132][C:129]1[CH:130]=[CH:131][C:126]([C:123]2[CH:122]=[CH:121][C:120]([NH:119][C:118]([C:114]3[CH:113]=[C:112]([S:109]([C:106]4[CH:107]=[C:108]5[C:103](=[C:104]([CH3:138])[CH:105]=4)[N:102]=[CH:101][C:100]([C:139]([NH2:141])=[O:140])=[C:99]5[NH:98][C:94]4[CH:95]=[CH:96][CH:97]=[C:92]([O:91][CH3:90])[CH:93]=4)(=[O:110])=[O:111])[CH:117]=[CH:116][CH:115]=3)=[O:137])=[CH:125][CH:124]=2)=[CH:127][CH:128]=1)([C:74]([CH3:77])([CH3:75])[CH3:76])([CH3:73])[CH3:72]

Participants

Reactant 3

HCID 66988956(R)-8-(2-amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one

HCID 866590984-((3-Methoxyphenyl)amino)-8-methyl-6-((3-((4'-(4-oxobutyl)-(1,1-biphenyl]-4-yl)carbamoyl)phenyl)sulfonyl)quinoline-3-carboxamide

HCID 86659116(R)-6-[[3-[[8-[[2-[(tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl]ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Product 1

HCID 86659117(R)-6-((3-((4'-(4-((2-((tert-butyldimethylsilyl)oxy)-2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)amino)butyl)-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 148, using (R)-8-(2-amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-5-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one in place of Intermediate 2 and Intermediate 124 in place of Intermediate 112. ES/MS calcd. for C57H63N6O9SSi+ 1035.4. Found m/z=1035.6 (M+H)+.

Sources & evidence

ORD record: ord-8fb8c278bdf1422189c73c0cce382aa2
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394829B2

Reaction notes

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