HCID 387663, compound → HCID 387662, compound

HRID 369510Notes

Reaction equation

HRID 369510 reaction equation
C([O-])(=O)C.[Na+].[F:6][C:7]([F:32])([F:31])[CH2:8][O:9][C:10]1[C:11]([OH:30])=[CH:12][C:13]2[C:14](=O)[CH2:15][C@@H:16]3[C@@H:25]([C:26]=2[CH:27]=1)[CH2:24][CH2:23][C@@:21]1([CH3:22])[C@H:17]3[CH2:18][CH2:19][C@@H:20]1[OH:28].Cl.[NH2:34][OH:35]>CO.O>[F:6][C:7]([F:32])([F:31])[CH2:8][O:9][C:10]1[C:11]([OH:30])=[CH:12][C:13]2[C:14](=[N:34][OH:35])[CH2:15][C@@H:16]3[C@@H:25]([C:26]=2[CH:27]=1)[CH2:24][CH2:23][C@@:21]1([CH3:22])[C@H:17]3[CH2:18][CH2:19][C@@H:20]1[OH:28]

Participants

6

Reactant 3

HCID 387663HCID 387663, compoundHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 387662HCID 387662, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Sodium acetate (2.86 g, 35 mmol) was added to a stirred solution of 6-oxo derivative (9) (0.45 g, 1.2 mmol) in methanol (55 mL). Hydroxylamine hydrochloride salt (2.2 g, 32 mmol) in water (3 mL) was then added at room temperature. The resulting mixture was stirred at 90° C. for 6 h. Then solvent was removed under reduced pressure, the resulting residue was diluted with water (60 mL), and product was extracted into ethyl acetate (3×120 mL). The combined organic layer was washed with water (70 mL), brine (70 mL), and dried over anhydrous sodium sulfate. The organic layer on evaporation under reduced pressure provided the crude product, which on crystallization from ethyl acetate-hexane mixture gave oxime (12) (0.3 g, 65%): mp 187-191° C.; IR (KBr) 3330, 2960-2860, 1500, 880, 750 cm-1 ; 1H NMR (CDCl3 +DMSO-d6 +D2O) δ 0.77 (s, 3 H), 1.10-2.38 (m, 11 H), 2.67 (s, 2 H), 3.05-3.27 (m, 2 H), 3.72 (t, J=8.5 Hz, 1 H), 4.50 (q, J=8.5 Hz, 2 H), 6.88 (s, 1 H), 7.57 (s, 1 H) 10.20 (s, 1 H). Anal. (C20H24NF3O4) C, H.

Workup

  1. customThen solvent was removed under reduced pressure
  2. additionthe resulting residue was diluted with water (60 mL), and product
  3. extractionwas extracted into ethyl acetate (3×120 mL)
  4. washThe combined organic layer was washed with water (70 mL), brine (70 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe organic layer on evaporation under reduced pressure
  7. customprovided the crude product, which
  8. customon crystallization from ethyl acetate-hexane mixture

Sources & evidence

ORD record
ord-c4cbd852e8b0469da33647da43a79b06
Source dataset
uspto-grants-2000_10
Patent number
US06136992

Reaction notes

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