(R)-4-(2-Amino-1-hydroxyethyl)-2-[[(tert-butyldimethylsilyl)oxy]methyl]phenol → (R)-6-[[3-[[4-[5-[[2-[3-[[(tert-Butyldimethylsilyl)oxy]methyl]-4-hydroxyphenyl]-2-hydroxyethyl]amino]pentyl]phenyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

HRID 1944969Notes

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

Participants

Reactant 3

HCID 58505193(R)-4-(2-Amino-1-hydroxyethyl)-2-[[(tert-butyldimethylsilyl)oxy]methyl]phenol

HCID 585052434-[(3-Methoxyphenyl)amino]-8-methyl-6-[[3-[[4-(5-oxopentyl)phenyl]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 58505142(R)-6-[[3-[[4-[5-[[2-[3-[[(tert-Butyldimethylsilyl)oxy]methyl]-4-hydroxyphenyl]-2-hydroxyethyl]amino]pentyl]phenyl]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 Intermediate 9 in place of Intermediate 2 and Intermediate 120 in place of Intermediate 112. ES/MS calcd. for C51H62N5O8SSi+ 932.40. Found m/z=932.4 (M+H)+.

Sources & evidence

ORD record: ord-ab937c7fcf5a4594a4b379b7eb8c233b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394829B2

Reaction notes

Loading…