(S)-3-(4'-chloro,-biphenyl-4-yl)-2-{[(3R,7S)-3-(4-hydroxy-phenyl)-1-methyl-2-oxo-6-((S)-1-phenyl-propyl)-2,3,5,6,7,8-hexahydro-1H-4-oxa-1,6-diaza-anthracene-7-carbonyl]-amino}-propionic acid methyl ester → HCID 59337471, compound

HRID 1711459Notes

Reaction equation

HRID 1711459 reaction equation
COC(=O)[C@@H](NC([C@@H]1CC2C=C3C(O[C@H](C4C=CC(O)=CC=4)C(=O)N3C)=CC=2CN1[C@H](C1C=CC=CC=1)CC)=O)CC1C=CC(C2C=CC(Cl)=CC=2)=CC=1.C[O:56][C:57](=[O:117])[C@@H:58]([NH:73][C:74]([C@@H:76]1[CH2:89][C:88]2[CH:87]=[C:86]3[C:81]([O:82][C@H:83]([C:92]4[CH:97]=[CH:96][C:95]([O:98][CH2:99][C:100]5[CH:105]=[CH:104][C:103]([Cl:106])=[C:102]([Cl:107])[CH:101]=5)=[CH:94][CH:93]=4)[C:84](=[O:91])[N:85]3[CH3:90])=[CH:80][C:79]=2[CH2:78][N:77]1[C@H:108]([C:111]1[CH:116]=[CH:115][CH:114]=[CH:113][CH:112]=1)[CH2:109][CH3:110])=[O:75])[CH2:59][C:60]1[CH:65]=[CH:64][C:63]([C:66]2[CH:71]=[CH:70][C:69]([Cl:72])=[CH:68][CH:67]=2)=[CH:62][CH:61]=1>>[Cl:72][C:69]1[CH:70]=[CH:71][C:66]([C:63]2[CH:62]=[CH:61][C:60]([CH2:59][C@H:58]([NH:73][C:74]([C@@H:76]3[CH2:89][C:88]4[CH:87]=[C:86]5[C:81]([O:82][C@H:83]([C:92]6[CH:97]=[CH:96][C:95]([O:98][CH2:99][C:100]7[CH:105]=[CH:104][C:103]([Cl:106])=[C:102]([Cl:107])[CH:101]=7)=[CH:94][CH:93]=6)[C:84](=[O:91])[N:85]5[CH3:90])=[CH:80][C:79]=4[CH2:78][N:77]3[C@H:108]([C:111]3[CH:112]=[CH:113][CH:114]=[CH:115][CH:116]=3)[CH2:109][CH3:110])=[O:75])[C:57]([OH:117])=[O:56])=[CH:65][CH:64]=2)=[CH:67][CH:68]=1

Participants

3

Reactant 2

HCID 66922815(S)-3-(4'-chloro,-biphenyl-4-yl)-2-{[(3R,7S)-3-(4-hydroxy-phenyl)-1-methyl-2-oxo-6-((S)-1-phenyl-propyl)-2,3,5,6,7,8-hexahydro-1H-4-oxa-1,6-diaza-anthracene-7-carbonyl]-amino}-propionic acid methyl esterHCID 86636870HCID 86636870, compound

Product 1

HCID 59337471HCID 59337471, compoundYield 88%

Procedure

(S)-3-(4′-chloro, -biphenyl-4-yl)-2-{[(3R,7S)-3-(4-hydroxy-phenyl)-1-methyl-2-oxo-6-((S)-1-phenyl-propyl)-2,3,5,6,7,8-hexahydro-1H-4-oxa-1,6-diaza-anthracene-7-carbonyl]-amino}-propionic acid methyl ester (74 mg) was converted to (S)-3-(4′-chloro-biphenyl-4-yl)-2-{[(3R,7S)-3-[4-(3,4-dichloro-benzyloxy)-phenyl]-1-methyl-2-oxo-6-((S)-1-phenyl-propyl)-2,3,5,6,7,8-hexahydro-1H-4-oxa-1,6-diaza-anthracene-7-carbonyl]-amino}-propionic acid methyl ester (60 mg) using general procedure K. This ester upon hydrolysis furnished title compound (52 mg) using general procedures B. LC-MS (m/z): 888.

Sources & evidence

ORD record
ord-fef7284798784380bba6f1aed6b3aeff
Source dataset
uspto-grants-2010_09
Patent number
US07790714B2

Reaction notes

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