Diethyl Ether → (S)-N-methyl-N-methoxy 2(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropyl)benzamide

HRID 249046Notes

Reaction equation

HRID 249046 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([OH:33])[CH2:21][CH2:22][C:23]4[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=4[C:25](OC)=[O:26])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.Cl.[CH3:35][NH:36][O:37][CH3:38].CC[Mg+].[Br-].CCOCC>C1COCC1>[CH3:35][N:36]([O:37][CH3:38])[C:25](=[O:26])[C:24]1[CH:29]=[CH:30][CH:31]=[CH:32][C:23]=1[CH2:22][CH2:21][C@@H:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH:13]=[CH:12][C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)[CH:15]=1)[OH:33]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 540063032-[3-(S)-[3-(2-(7-Chloro-2-quinolinyl)(E/Z)ethenyl)phenyl]-3-hydroxypropyl]benzoic acid methyl esterHCID 178461630HCID 178461630, compound

Product 1

HCID 53651148(S)-N-methyl-N-methoxy 2(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropyl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of the hydroxy ester of Step 3 (4.519 g, 9.5 mmol) and N,O-dimethylhydroxylamine hydrochloride (2.777 g, 28.5 mmol) in 95 mL of anhydrous THF at 0° C. was added dropwise 3M EtMgBr in Et2O (22 mL 66 mmol) over ≃40 min. The mixture was then stirred at 0° C. for 30 min. and poured into ice-cold saturated NH4Cl. The product was extracted in EtOAc, dried over Na2SO4, and concentrated to yield the title compound.

Workup

  1. additionpoured into ice-cold saturated NH4Cl
  2. extractionThe product was extracted in EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-00bde7c936de4cdfae0bb11dbb63c4c1
Source dataset
uspto-grants-1993_05
Patent number
US05212180

Reaction notes

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