Hydrochloric Acid → HCID 72516191, compound

HRID 1836513Notes

Reaction equation

HRID 1836513 reaction equation
CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[O:11][CH2:12][C:13]([OH:15])=[O:14])=[O:9])[C:4](=[O:24])[O:3]1.[OH-].[Li+].Cl>O1CCCC1>[C:13]([CH2:12][O:11][N:10]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[C:8]([CH:7]=[C:5]([OH:6])[C:4]([OH:24])=[O:3])=[O:9])([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 74058487HCID 74058487, compound

Product 1

HCID 72516191HCID 72516191, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [[2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-acetyl]-(4-fluorobenzyl)-aminooxy]-acetic acid (0.20 g, 0.56 mmol) in tetrahydrofuran (5 ml) was treated at 0° C. with 1.7 ml (1.7 mmol) of 1 M aqueous lithium hydroxide. After 2 h, the reaction mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried (magnesium sulphate) and evaporated in vacuo. Crystallisation of the residual solid from a mixture of ethyl acetate and hexane gave 0.083 g (47% yield) of the title material as a white solid: mp 135-138° C. 1HNMR 400 MHz (DMSO-d6) δ (ppm): (mixture of enol and keto forms, 7:3); enol form: 4.65 (2H, s, CH2), 4.92 (2H, s, CH2), 6.51 (1H, s, CH), 7.18 (2H, m, aromatics), 7.37 (2H, m, aromatics), 13.17 (1H, broad, OH). Anal. calcd for C13H12FNO7: C, 49.85; H, 3.86; N, 4.47. Found: C, 49.83; H, 3.90; N, 4.37.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated in vacuo
  5. customCrystallisation of the residual solid
  6. additionfrom a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-fe5157eb45b44540a1df3a3b62cdf16b
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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