2-Methoxyethyl chloroformate → HCID 58758461, compound

HRID 459032Notes

Reaction equation

HRID 459032 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.Cl[C:34]([O:36][CH2:37][CH2:38][O:39][CH3:40])=[O:35]>CN(C=O)C.N1C=CC=CC=1.O>[C:34](=[O:35])([O:36][CH2:37][CH2:38][O:39][CH3:40])[O:20][CH2:19][C@H:17]1[O:16][N:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]3[CH:6]=[CH:5][C:4]([N:21]4[CH2:25][C@H:24]([CH2:26][N:27]5[CH:31]=[CH:30][N:29]=[N:28]5)[O:23][C:22]4=[O:32])=[CH:3][C:2]=3[F:1])=[CH:9][N:10]=2)[CH2:18]1

Participants

6

Reactant 2

HCID 694002-Methoxyethyl chloroformate2×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 58758461HCID 58758461, compoundYield 80.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

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, 0.2 g, 0.46 mmol) was dissolved in DMF (4 ml) and pyridine (0.5 ml), then cooled to 0° C. 2-Methoxyethyl chloroformate (0.2 ml, 1.73 mmol) was added, the mixture was stirred at 0° C. for 45 minutes followed by addition of a second portion of 2-methoxyethyl chloroformate. The mixture was stirred for one additional hour at 0° C., then diluted with water, extracted twice with ethyl acetate and dried over sodium sulfate. The residue obtained upon filtration and evaporation was purified via chromatography (silica gel, 0 to 10% acetonitrile in ethyl acetate). Evaporation of the product containing fractions and trituration of the resulting solid with diethyl ether yielded the title compound as a white solid (0.20 g), melting point: 112° C.

Workup

  1. stirringThe mixture was stirred for one additional hour at 0° C.
  2. extractionextracted twice with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe residue obtained upon filtration and evaporation
  5. customwas purified via chromatography (silica gel, 0 to 10% acetonitrile in ethyl acetate)
  6. customEvaporation of the product
  7. additioncontaining fractions and trituration of the resulting solid with diethyl ether

Sources & evidence

ORD record
ord-cf81c36191274777a28554a7c3dd6da3
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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