1-(Chloromethoxy)-2-methoxyethane → HCID 58822466, compound

HRID 459056Notes

Reaction equation

HRID 459056 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][C@H:24]([CH2:26][N:27]3[CH:31]=[CH:30][N:29]=[N:28]3)[O:23][C:22]2=[O:32])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([C:14]2[CH2:18][C@@H:17]([CH2:19][OH:20])[O:16][N:15]=2)=[CH:12][CH:13]=1.C(N(C(C)C)CC)(C)C.[CH3:42][O:43][CH2:44][CH2:45][O:46][CH2:47]Cl>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][C@H:24]([CH2:26][N:27]3[CH:31]=[CH:30][N:29]=[N:28]3)[O:23][C:22]2=[O:32])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([C:14]2[CH2:18][C@@H:17]([CH2:19][O:20][CH2:42][O:43][CH2:44][CH2:45][O:46][CH3:47])[O:16][N:15]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 775901-(Chloromethoxy)-2-methoxyethane3×HCID 81531Diisopropylethylamine2×HCID 9932836(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

Product 1

HCID 58822466HCID 58822466, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 1: 250 mg, 0.57 mmol), diisopropyl ethyl amine (238 μL, 1.37 mmol) and 2-methoxyethoxymethyl chloride (MEMCI) (78 μL, 0.68 mmol) were mixed in dry DMF (5 mL) and stirred at room temperature overnight. More diisopropyl ethylamine (250 μL, 1.44 mmol) and MEMCl (100 μL, 0.88 mmol) were added and it was stirred for another 6 hours. Again MEMCl (90 μL, 0.79 mmol) was added and it was stirred overnight. The solvent was evaporated under reduced pressure. Chromatography on silica gel with acetone/hexanes 3:1 and precipitation from dichloromethane/hexanes gave the product as off-white solid (261 mg).

Workup

  1. stirringit was stirred for another 6 hours
  2. stirringit was stirred overnight
  3. customThe solvent was evaporated under reduced pressure
  4. customChromatography on silica gel with acetone/hexanes 3:1 and precipitation from dichloromethane/hexanes

Sources & evidence

ORD record
ord-b27cc7902d024e0e82f7c8fa2093d76b
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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