Diethyl Ether → HCID 178458448, compound

HRID 1633734Notes

Reaction equation

HRID 1633734 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([C:8]2[CH:9]=[C:10]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)=[O:7])[N:3]=[CH:2]1.[CH2:20]([Mg]Br)[CH3:21].CCOCC>C1COCC1>[OH:7][C:6]([C:8]1[CH:9]=[C:10]([NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])[CH:11]=[CH:12][CH:13]=1)([C:4]1[N:3]=[CH:2][NH:1][CH:5]=1)[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 178418443HCID 178418443, compoundHCID 178477715HCID 178477715, compound

Product 1

HCID 178458448HCID 178458448, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 55E (84 mg, 0.3 mmol) in THF (10 mL) at 0° C. was added dropwise a 2M solution of ethyl magnesium bromide in ether (0.6 mL, 1.2 mmol) and the resulting mixture was allowed to warm to room temperature for 6 hours. The mixture was quenched with saturated NH4Cl and concentrated under vacuum. The residue was passed through a Dowex® 50×8-400 ion exchange resin with 5% NH4OH as eluent. The ammonia solution was concentrated under vacuum and purified again by chromatography (silica gel, 9:1 CH2Cl2:ethanol) to provide 20 mg of the desired product.

Workup

  1. customThe mixture was quenched with saturated NH4Cl
  2. concentrationconcentrated under vacuum
  3. concentrationThe ammonia solution was concentrated under vacuum
  4. custompurified again by chromatography (silica gel, 9:1 CH2Cl2:ethanol)

Sources & evidence

ORD record
ord-ca4a384ec551408cb916bb040153bf24
Source dataset
uspto-grants-2003_01
Patent number
US06503935B1

Reaction notes

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