1-Deoxy-1-(methylamino)hexitol → 1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-{5-[methyl-(2,3,4,5,6-pentahydroxyhexyl)amino]pentyloxy}phenyl)azetidin-2-one

HRID 2104920Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]I)=[CH:14][CH:13]=3)[CH:10]([CH2:25][CH2:26][CH:27]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[OH:28])[C:9]2=[O:36])=[CH:4][CH:3]=1.[CH3:37][NH:38][CH2:39][CH:40]([OH:49])[CH:41]([OH:48])[CH:42]([OH:47])[CH:43]([OH:46])[CH2:44][OH:45]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:38]([CH3:37])[CH2:39][CH:40]([OH:49])[CH:41]([OH:48])[CH:42]([OH:47])[CH:43]([OH:46])[CH2:44][OH:45])=[CH:14][CH:13]=3)[CH:10]([CH2:25][CH2:26][CH:27]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[OH:28])[C:9]2=[O:36])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

170 mg of 1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(5-iodopentyloxy)phenyl]azetidin-2-one are dissolved in 5 ml of absolute dimethylformamide. 220 mg of 6-methylaminohexane-1,2,3,4,5-pentaol are then added, and the reaction solution is stirred at 50° C. for 2 h. After concentration using a rotary evaporator and oil pump vacuum at 40° C., the residue is purified by preparative HPLC. The product is obtained as an oil. C36H46F2N2O8 (672) MS (ESI): M+

Workup

concentrationAfter concentration
customa rotary evaporator and oil pump vacuum at 40° C.
customthe residue is purified by preparative HPLC
customThe product is obtained as an oil

Sources & evidence

ORD record: ord-708f03ab94ee494fbde9369227d65195
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576200B2

Reaction notes

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