Hydrochloric Acid → HCID 72516187, compound

HRID 1836503Notes

Reaction equation

HRID 1836503 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][N:9]([C:18](=[O:28])[CH:19]=[C:20]1[C:24](=[O:25])[O:23]C(C)(C)[O:21]1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl.C(#N)C>O1CCCC1.O>[C:1]([O:5][C:6]([CH2:7][O:8][N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)[C:18]([CH:19]=[C:20]([OH:21])[C:24]([OH:25])=[O:23])=[O:28])=[O:29])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6342AcetonitrileHCID 74058492HCID 74058492, compound

Product 1

HCID 72516187HCID 72516187, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [[2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-acetyl]-(4-fluorobenzyl)-aminooxy]-acetic acid tert-butyl ester (0.10 g, 0.24 mmol) in tetrahydrofuran (3 ml) was treated at 0° C. with 0.48 ml (0.48 mmol) of 1 M aqueous lithium hydroxide. After 1 h, the reaction mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with brine, dried (magnesium sulphate) and evaporated in vacuo. Chromatograpy of the residual solid on Premisphere 5 μC-8 (gradient of acetonitrile in water) gave 0.037 g (41% yield) of the title material as a white solid: mp 73° C. (dec). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.51 (9H, s t-Bu), 4.36 (2H, s, CH2), 4.95 (2H, s, CH2), 6.66 (1H, broad s, CH), 7.05 (2H, m, aromatics), 7.39 (2H, m, aromatics). HRMS (ES+) calculated for C17H21FNO7[M+H]+: 370.130206. Found: 370.129173.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-0510503ceab8434d99e25ff4273d8a98
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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