Sodium Iodide → (5-methyl-2-oxo-[1,3]dioxol-4-yl)methyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoate

HRID 1779151Notes

Reaction equation

HRID 1779151 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([F:48])([F:47])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@@:22]([OH:30])([CH2:26][CH2:27][O:28][CH3:29])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[I-].[Na+].C(=O)(O)[O-].[Na+].Cl[CH2:57][C:58]1[O:59][C:60](=[O:64])[O:61][C:62]=1[CH3:63]>CN(C=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:31]=[CH:32]/[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]([F:47])([F:48])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C@@:22]([OH:30])([CH2:26][CH2:27][O:28][CH3:29])[C:23]([O:25][CH2:57][C:58]2[O:59][C:60](=[O:64])[O:61][C:62]=2[CH3:63])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 98555184-(Chloromethyl)-5-methyl-1,3-dioxol-2-oneHCID 60150052(E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid

Product 1

HCID 60149012(5-methyl-2-oxo-[1,3]dioxol-4-yl)methyl (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoateYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the mixture of (E)-(2S,3S)-3-[(S)-2-(4-butoxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoic acid (No. 5514403, 50 mg, 0.0731 mmol), sodium iodide (16.4 mg, 0.110 mmol), sodium bicarbonate (7.4 mg, 0.877 mmol) and the DMF (1 mL) was added commercially available 4-chloromethyl-5-methyl-1,3-dioxol-2-one (15.9 μL, 0.145 mmol) at room temperature, and the mixture was stirred as it was for 22 hours. After confirming the consumption of the starting materials by LCMS, the reaction solution was filtered through a syringe filter, and purified as it was by preparative HPLC. The purified fraction was freeze-dried to obtain the title compound (48 mg, 83% yield) as yellow oil.

Workup

  1. customthe consumption of the starting materials by LCMS
  2. filtrationthe reaction solution was filtered through a syringe
  3. filtrationfilter
  4. custompurified as it
  5. customThe purified fraction was freeze-dried

Sources & evidence

ORD record
ord-6ef62b1ca5124b25a9ad18efe69375b2
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

Loading…