Dimethylformamide → N-[5-(3-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]4-oxoazetidin-2-yl}phenylcarbamoyl)pentyl]-2,3,4,5,6-pentahydroxyhexanamide

HRID 2104906Notes

Reaction equation

HRID 2104906 reaction equation
NC[C:3]1[CH:4]=[C:5]([CH:9]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:11](=[O:20])[CH:10]2[CH2:21][CH2:22][CH:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[OH:24])[CH:6]=[CH:7][CH:8]=1.[OH:32][CH:33]([CH:58]([OH:65])[CH:59]([OH:64])[CH:60]([OH:63])[CH2:61][OH:62])[C:34](=[O:57])COCCOCCNC(COCCOCCOCC(O)=O)=O.C(N=C=NC(C)C)(C)C.O[C:76]1[C:84]2[N:83]=N[NH:81][C:80]=2[CH:79]=[CH:78][CH:77]=1.CN(C)C=[O:88]>>[F:19][C:16]1[CH:15]=[CH:14][C:13]([N:12]2[C:11](=[O:20])[CH:10]([CH2:21][CH2:22][CH:23]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[OH:24])[CH:9]2[C:5]2[CH:4]=[C:3]([NH:83][C:84]([CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][NH:81][C:34](=[O:57])[CH:33]([OH:32])[CH:58]([OH:65])[CH:59]([OH:64])[CH:60]([OH:63])[CH2:61][OH:62])=[O:88])[CH:8]=[CH:7][CH:6]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 12734DiisopropylcarbodiimideHCID 222520374-(3-Aminomethylphenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-oneHCID 22252092{2-[2-({2-[2-(3,4,5,6,7-Pentahydroxy-2-oxoheptyloxy)ethoxy]ethylcarbamoyl]methoxy)ethoxy]ethoxy}acetic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 22252088N-[5-(3-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]4-oxoazetidin-2-yl}phenylcarbamoyl)pentyl]-2,3,4,5,6-pentahydroxyhexanamide

Procedure

29 is prepared similarly to 18 starting from 62 mg of 4-(3-aminomethylphenyl)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-hydroxypropyl]azetidin-2-one 15, 76 mg of {2-[2-({2-[2-(3,4,5,6,7-pentahydroxy-2-oxoheptyloxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethoxy}acetic acid 26, 57 μl of diisopropylcarbodiimide and 40 mg of hydroxybenzotriazole in 2 ml of dimethylformamide. This gives 19:

Sources & evidence

ORD record
ord-5e3b50215f5a4d0ca21c69f90a2b26ea
Source dataset
uspto-grants-2009_08
Patent number
US07576200B2

Reaction notes

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