Water → HCID 60054148, compound

HRID 488374Notes

Reaction equation

HRID 488374 reaction equation
[CH2:1]1[C:6]2[CH:7]=[C:8]([N:11]3[CH2:15][C@H:14]([CH2:16][NH:17][C:18](=[O:20])[CH3:19])[O:13][C:12]3=[O:21])[CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][S:2]1.[OH2:22]>CO.[Cl-].[Na+].O>[O:22]=[S:2]1[CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:15][C@H:14]([CH2:16][NH:17][C:18](=[O:20])[CH3:19])[O:13][C:12]3=[O:21])=[CH:7][C:6]=2[CH2:1]1

Participants

5

Reactant 2

HCID 962WaterHCID 60054147HCID 60054147, compound

Product 1

HCID 60054148HCID 60054148, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of NaIO4 (220 mg, 1.03 mmol) in H2O (4.1 mL) is treated with a solution of (−)-N-[[(5S)-3-(3,4-dihydro-1H-2-benzothiopyran-7-yl)-2-oxo-5-oxazolidinyl]methyl]acetamide (Example 14, 300 mg, 0.979 mmol) in MeOH (20 mL) over approximately 1 min, and the resulting mixture is stirred at ambient temperature for 18 hrs. The mixture is then diluted with brine (25 mL) and extracted with 10% MeOH/CH2Cl2 (4×25 mL), and the combined organic phase is dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue is chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with a gradient of MeOH/CH2Cl2 (2/98-8/92), and those fractions with an Rf=0.20 by TLC (MeOH/CHCl3, 10/90) are pooled and concentrated to give 293 mg (93%) of the title compound (mixture of diastereomers) as an amorphous, white solid.

Workup

  1. extractionextracted with 10% MeOH/CH2Cl2 (4×25 mL)
  2. dry with materialthe combined organic phase is dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge
  5. washeluting with a gradient of MeOH/CH2Cl2 (2/98-8/92)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-76d3280739924f1395c9bdffcee84dee
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

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