(S)-N-((S)-1-(((2R,4S)-1,2-dihydroxy-2,6-dimethyl-3-oxoheptan-4-yl)amino)-1-oxo-3-phenylpropan-2-yl)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide → (4S,7S,10S,13S)-10-Benzyl-15-hydroxy-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-3,6,9,12-tetraazahexadecan-16-yl 2,4-dimethoxy-6-(prop-2-yn-1-yloxy)benzenesulfonate

HRID 630617Notes

Reaction equation

C(NC(C1C=C(S(OC[C@](O)(C)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CC2C=CC=CC=2)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC2C=CC=CC=2)NC(=O)CN2CCOCC2)(=O)=O)C=CC=1)=O)C#C.[CH3:69][O:70][C:71]1[CH:76]=[C:75]([O:77][CH3:78])[CH:74]=[C:73]([O:79][CH2:80][C:81]#[CH:82])[C:72]=1[S:83](Cl)(=[O:85])=[O:84].[OH:87][CH2:88][C@:89]([OH:139])([CH3:138])[C:90](=[O:137])[C@@H:91]([NH:96][C:97](=[O:136])[C@@H:98]([NH:106][C:107](=[O:135])[C@@H:108]([NH:113][C:114](=[O:134])[C@@H:115]([NH:124][C:125](=[O:133])[CH2:126][N:127]1[CH2:132][CH2:131][O:130][CH2:129][CH2:128]1)[CH2:116][CH2:117][C:118]1[CH:123]=[CH:122][CH:121]=[CH:120][CH:119]=1)[CH2:109][CH:110]([CH3:112])[CH3:111])[CH2:99][C:100]1[CH:105]=[CH:104][CH:103]=[CH:102][CH:101]=1)[CH2:92][CH:93]([CH3:95])[CH3:94]>>[CH3:69][O:70][C:71]1[CH:76]=[C:75]([O:77][CH3:78])[CH:74]=[C:73]([O:79][CH2:80][C:81]#[CH:82])[C:72]=1[S:83]([O:87][CH2:88][C:89]([OH:139])([CH3:138])[C:90](=[O:137])[C@H:91]([CH2:92][CH:93]([CH3:94])[CH3:95])[NH:96][C:97](=[O:136])[C@H:98]([CH2:99][C:100]1[CH:105]=[CH:104][CH:103]=[CH:102][CH:101]=1)[NH:106][C:107](=[O:135])[C@H:108]([CH2:109][CH:110]([CH3:112])[CH3:111])[NH:113][C:114](=[O:134])[C@H:115]([CH2:116][CH2:117][C:118]1[CH:119]=[CH:120][CH:121]=[CH:122][CH:123]=1)[NH:124][C:125](=[O:133])[CH2:126][N:127]1[CH2:132][CH2:131][O:130][CH2:129][CH2:128]1)(=[O:84])=[O:85]

Participants

Reactant 3

HCID 86715358(S)-N-((S)-1-(((2R,4S)-1,2-dihydroxy-2,6-dimethyl-3-oxoheptan-4-yl)amino)-1-oxo-3-phenylpropan-2-yl)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide

HCID 86715390(4S,7S,10S,13S,15R)-10-Benzyl-15-hydroxy-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-3,6,9,12-tetraazahexadecan-16-yl 3-(prop-2-yn-1-ylcarbamoyl)benzenesulfonate

HCID 867153922,4-Dimethoxy-6-(prop-2-yn-1-yloxy)benzene-1-sulfonyl chloride

Product 1

HCID 86715391(4S,7S,10S,13S)-10-Benzyl-15-hydroxy-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-3,6,9,12-tetraazahexadecan-16-yl 2,4-dimethoxy-6-(prop-2-yn-1-yloxy)benzenesulfonate

Procedure

Prepared in a similar manner to compound 13, except from 2,4-dimethoxy-6-(prop-2-yn-1-yloxy)benzene-1-sulfonyl chloride and (S)—N—((S)-1-(((2R,4S)-1,2-dihydroxy-2,6-dimethyl-3-oxoheptan-4-yl)amino)-1-oxo-3-phenylpropan-2-yl)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamide.

Sources & evidence

ORD record: ord-02d784fc3b394cedac0b74b948f02e5a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315542B2

Reaction notes

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