(R)-8-(2-amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-6-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one → (R)-6-((11-((2-((tert-butyldimethylsilyl)oxy)-2-(6-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)amino)undecyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

HRID 1944974Notes

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[CH:81]=[C:80]([OH:89])[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]([CH3:124])[CH:105]=[C:106]([S:109]([CH2:112][CH2:113][CH2:114][CH2:115][CH2:116][CH2:117][CH2:118][CH2:119][CH2:120][CH2:121][CH:122]=O)(=[O:111])=[O:110])[CH:107]=3)[N:102]=[CH:101][C:100]=2[C:125]([NH2:127])=[O:126])[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[CH:81]=[C:80]([OH:89])[CH:79]=1)[CH2:68][NH:67][CH2:122][CH2:121][CH2:120][CH2:119][CH2:118][CH2:117][CH2:116][CH2:115][CH2:114][CH2:113][CH2:112][S:109]([C:106]1[CH:107]=[C:108]2[C:103](=[C:104]([CH3:124])[CH:105]=1)[N:102]=[CH:101][C:100]([C:125]([NH2:127])=[O:126])=[C:99]2[NH:98][C:94]1[CH:95]=[CH:96][CH:97]=[C:92]([O:91][CH3:90])[CH:93]=1)(=[O:111])=[O:110])([C:74]([CH3:77])([CH3:75])[CH3:76])([CH3:73])[CH3:72]

Participants

Reactant 3

HCID 66988084(R)-8-(2-amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-6-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one

HCID 86659100HCID 86659100, compound

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 66988392(R)-6-((11-((2-((tert-butyldimethylsilyl)oxy)-2-(6-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)amino)undecyl)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)-6-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one in place of Intermediate 2 and Intermediate 126 in place of Intermediate 112. ES/MS calcd. for C45H64N5O8SSi+ 862.4. Found m/z=862.6 (M+H)+.

Sources & evidence

ORD record: ord-626d6352112949889f575fa441abfab1
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394829B2

Reaction notes

Loading…