Hydrochloric Acid → HCID 60054146, compound

HRID 488362Notes

Reaction equation

HRID 488362 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N:18]3[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]3=[O:28])[CH:14]=2)[CH2:9]1)=[O:7])(=O)C.C([O-])([O-])=O.[K+].[K+].Cl>CO>[OH:4][CH2:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N:18]3[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]3=[O:28])[CH:14]=2)[CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60054136HCID 60054136, compound

Product 1

HCID 60054146HCID 60054146, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-[[(5S)-3-[2-[(acetyloxy)acetyl]-1,2,3,4-tetrahydro-6-isoquinolinyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (Example 3, 230 mg, 0.591 mmol) in MeOH (5.9 mL) is treated with K2CO3 (163 mg, 1.18 mmol), and the resulting mixture is stirred at ambient temperature for 1 hr and is then adjusted to pH 7 with 1M aqueous HCl and concentrated under reduced pressure. The residue is diluted with brine (10 mL) and extracted with CH2Cl2 (3×20 mL), and the combined organic phase is dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product is then chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with a gradient of MeOH/CH2Cl2 (2/98-5/95), and those fractions with an Rf=0.25 by TLC (MeOH/CHCl3, 10/90) are pooled and concentrated and the residue triturated with Et2O to give 146 mg (71%) of the title compound as an amorphous, white solid. MS (ESI+) for C17H21N3O5 m/z 348 (M+H)+; [α]25D=−18° (c 0.96, DMSO); Anal. Calcd for C17H21N3O5: C, 58.78; H, 6.09; N, 12.10. Found: C, 58.59; H, 6.49; N, 11.77.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue is diluted with brine (10 mL)
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. dry with materialthe combined organic phase is dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is then chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge
  7. washeluting with a gradient of MeOH/CH2Cl2 (2/98-5/95)
  8. concentrationconcentrated
  9. customthe residue triturated with Et2O

Sources & evidence

ORD record
ord-643691b941034868a78e8b778d5f03a3
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

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