Dimethylamine → HCID 73855551, compound

HRID 1836508Notes

Reaction equation

HRID 1836508 reaction equation
[CH3:1][C:2]1([CH3:25])[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](O)=[O:14])=[O:9])[C:4](=[O:24])[O:3]1.C(Cl)(=O)C(Cl)=O.[CH3:32][NH:33][CH3:34].N1C=CC=CC=1>ClCCl.C(OCC)(=O)C.CN(C)C=O>[CH3:32][N:33]([CH3:34])[C:13]([CH2:12][O:11][N:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:8](=[O:9])[CH:7]=[C:5]1[C:4](=[O:24])[O:3][C:2]([CH3:25])([CH3:1])[O:6]1)=[O:14]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 1049PyridineHCID 65578Oxalyl chlorideHCID 74058487HCID 74058487, compound

Product 1

HCID 73855551HCID 73855551, compoundYield 50.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution [[2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-acetyl]-(4-fluorobenzyl)-aminooxy]-acetic acid (0.681 g, 1.93 mmol) in dichloromethane (20 ml) was treated at 22° C. with oxalyl chloride (0.34 ml, 3.9 mmol) and a trace of N,N-dimethylformamide and the resulting mixture was stirred for 1 h. The solvent and excess reagent were then evaporated in vacuo. The residual material was dissolved in dry dichloromethane (10 ml) and added dropwise to a cold (0° C.) solution of dimethylamine (0.18 g, 4.0 mmol) and pyridine (0.25 ml, 3.2 mmol ) in dichloromethane. After 2 h, the reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate and brine and dried over anhydrous magnesium sulphate. Evaporation of the solvent in vacuo and crystallisation of the residue from a mixture of ethyl acetate and hexane gave 0.370 g (50% yield) of the title material as a white solid. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.77 (6H, s, CH3), 2.91 (3H, s, CH3), 2.97 (3H, s, CH3), 4.53 (2H, s, CH2), 4.93 (2H, s, CH2), 6.43 (1H, s, CH), 7.03 (2H, m, aromatics), 7.41 (2H, m, aromatics). HRMS (ES+) calculated for C18H22FN2O6[M+H]+: 381.146190. Found: 381.146382.

Workup

  1. customThe solvent and excess reagent were then evaporated in vacuo
  2. dissolutionThe residual material was dissolved in dry dichloromethane (10 ml)
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customEvaporation of the solvent
  6. customin vacuo and crystallisation of the residue
  7. additionfrom a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-63f16f789b0e48e6b7c67eea7cc88084
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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