Propargyl alcohol → (4S,7S,10S,13S)-10-Benzyl-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-15-(((prop-2 yn-1-yloxy)carbonyl)oxy)-3,6,9,12-tetraazahexadecan-16-yl methanesulfonate

HRID 628171Notes

Reaction equation

[C:1](=O)([O-:58])[O:2][CH:3]([C@](C)(CI)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CC1C=CC=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC1C=CC=CC=1)NC(=O)CN1CCOCC1)[C:4]#[CH:5].C(O)C#C.[CH3:64][S:65]([O:68][CH2:69][C@:70]([OH:120])([CH3:119])[C:71](=[O:118])[C@H:72]([CH2:114][CH:115]([CH3:117])[CH3:116])[NH:73][C:74](=[O:113])[C@H:75]([CH2:106][C:107]1[CH:112]=[CH:111][CH:110]=[CH:109][CH:108]=1)[NH:76][C:77](=[O:105])[C@H:78]([CH2:101][CH:102]([CH3:104])[CH3:103])[NH:79][C:80](=[O:100])[C@H:81]([CH2:92][CH2:93][C:94]1[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=1)[NH:82][C:83](=[O:91])[CH2:84][N:85]1[CH2:90][CH2:89][O:88][CH2:87][CH2:86]1)(=[O:67])=[O:66]>>[CH3:64][S:65]([O:68][CH2:69][C:70]([CH3:119])([O:120][C:1]([O:2][CH2:3][C:4]#[CH:5])=[O:58])[C:71](=[O:118])[C@H:72]([CH2:114][CH:115]([CH3:116])[CH3:117])[NH:73][C:74](=[O:113])[C@H:75]([CH2:106][C:107]1[CH:112]=[CH:111][CH:110]=[CH:109][CH:108]=1)[NH:76][C:77](=[O:105])[C@H:78]([CH2:101][CH:102]([CH3:104])[CH3:103])[NH:79][C:80](=[O:100])[C@H:81]([CH2:92][CH2:93][C:94]1[CH:99]=[CH:98][CH:97]=[CH:96][CH:95]=1)[NH:82][C:83](=[O:91])[CH2:84][N:85]1[CH2:86][CH2:87][O:88][CH2:89][CH2:90]1)(=[O:66])=[O:67]

Participants

Reactant 3

HCID 7859Propargyl alcohol

HCID 72737693(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 methanesulfonate

HCID 86715385(4S,7S,10S,13S,15S)-10-benzyl-16-iodo-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-3,6,9,12-tetraazahexadecan-15-ylprop-2-yn-1-yl carbonate

Product 1

HCID 86715384(4S,7S,10S,13S)-10-Benzyl-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-15-(((prop-2 yn-1-yloxy)carbonyl)oxy)-3,6,9,12-tetraazahexadecan-16-yl methanesulfonate

Procedure

Prepared according to the procedure for (4S,7S,10S,13S,15S)-10-benzyl-16-iodo-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-3,6,9,12-tetraazahexadecan-15-ylprop-2-yn-1-yl carbonate, except using propargyl alcohol and (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 methanesulfonate.

Workup

customPrepared

Sources & evidence

ORD record: ord-cfb61f5a9ccf4684be52e627fb8eaf16
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309283B2

Reaction notes

Loading…