(S)-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}-3-(4'-methoxy-biphenyl-4-yl)-propionic acid methyl ester → HCID 59337448, compound

HRID 2273428Notes

Reaction equation

HRID 2273428 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(OC)=CC=2)=CC=1.C[O:57][C:58](=[O:119])[C@@H:59]([NH:75][C:76]([C@@H:78]1[CH2:91][C:90]2[CH:89]=[C:88]3[C:83]([O:84][C@H:85]([C:94]4[CH:99]=[CH:98][C:97]([O:100][CH2:101][C:102]5[CH:107]=[CH:106][C:105]([Cl:108])=[C:104]([Cl:109])[CH:103]=5)=[CH:96][CH:95]=4)[C:86](=[O:93])[N:87]3[CH3:92])=[CH:82][C:81]=2[CH2:80][N:79]1[C@H:110]([C:113]1[CH:118]=[CH:117][CH:116]=[CH:115][CH:114]=1)[CH2:111][CH3:112])=[O:77])[CH2:60][C:61]1[CH:66]=[CH:65][C:64]([C:67]2[CH:72]=[CH:71][C:70]([O:73][CH3:74])=[CH:69][CH:68]=2)=[CH:63][CH:62]=1>>[Cl:109][C:104]1[CH:103]=[C:102]([CH:107]=[CH:106][C:105]=1[Cl:108])[CH2:101][O:100][C:97]1[CH:98]=[CH:99][C:94]([C@H:85]2[O:84][C:83]3[C:88](=[CH:89][C:90]4[CH2:91][C@@H:78]([C:76]([NH:75][C@@H:59]([CH2:60][C:61]5[CH:66]=[CH:65][C:64]([C:67]6[CH:68]=[CH:69][C:70]([O:73][CH3:74])=[CH:71][CH:72]=6)=[CH:63][CH:62]=5)[C:58]([OH:119])=[O:57])=[O:77])[N:79]([C@H:110]([C:113]5[CH:114]=[CH:115][CH:116]=[CH:117][CH:118]=5)[CH2:111][CH3:112])[CH2:80][C:81]=4[CH:82]=3)[N:87]([CH3:92])[C:86]2=[O:93])=[CH:95][CH:96]=1

Participants

3

Reactant 2

HCID 66922724(S)-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}-3-(4'-methoxy-biphenyl-4-yl)-propionic acid methyl esterHCID 66923185(S)-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}-3-(4'-methoxy-biphenyl-4-yl)-propionic acid methyl ester

Product 1

HCID 59337448HCID 59337448, compoundYield 92.1%

Procedure

(S)-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}-3-(4′-methoxy-biphenyl-4-yl)-propionic acid methyl ester was converted to (S)-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}-3-(4′-methoxy-biphenyl-4-yl)-propionic acid methyl ester (64 mg) using general procedure K. This ester upon hydrolysis furnished title compound (58 mg) LCMS (m/z): 884.

Sources & evidence

ORD record
ord-96357b477ea64165afbd036c7ee362b4
Source dataset
uspto-grants-2015_09
Patent number
US09120813B2

Reaction notes

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