1-Deoxy-1-(methylamino)hexitol → 1-(4-Fluorophenyl)-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-{8-[methyl-(2,3,4,5,6-pentahydroxyhexyl)amino]octyloxy}phenyl)azetidin-2-one

HRID 1612550Notes

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][CH2:24][CH2:25][CH2:26]I)=[CH:14][CH:13]=3)[CH:10]([CH2:28][CH2:29][CH:30]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[OH:31])[C:9]2=[O:39])=[CH:4][CH:3]=1.[CH3:40][NH:41][CH2:42][CH:43]([OH:52])[CH:44]([OH:51])[CH:45]([OH:50])[CH:46]([OH:49])[CH2:47][OH:48]>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][CH2:24][CH2:25][CH2:26][N:41]([CH3:40])[CH2:42][CH:43]([OH:52])[CH:44]([OH:51])[CH:45]([OH:50])[CH:46]([OH:49])[CH2:47][OH:48])=[CH:14][CH:13]=3)[CH:10]([CH2:28][CH2:29][CH:30]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[OH:31])[C:9]2=[O:39])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

150 mg of 1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(8-iodooctyloxy)phenyl]azetidin-2-one are dissolved in 5 ml of absolute dimethylformamide. 180 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. C39H52F2N2O8 (714) 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-8812552f2cb34ab49402321a7a96621b
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06992067B2

Reaction notes

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