Diethyl Ether → HCID 58124846, compound

HRID 1971643Notes

Reaction equation

HRID 1971643 reaction equation
CC[C:3]([C:5](Cl)=[O:6])=[O:4].[C:8]([NH:12][CH2:13][CH2:14][C:15]#[C:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)([CH3:11])([CH3:10])[CH3:9].C(N([CH2:27][CH3:28])CC)C.C([O:31]CC)C>C([O-])([O-])=O.[K+].[K+]>[C:8]([N:12]([CH2:13][CH2:14][C:15]#[C:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[C:3](=[O:4])[C:5]([O:6][CH2:27][CH3:28])=[O:31])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 8471TriethylamineHCID 11007880Butanoyl chloride, 2-oxo-HCID 58124810HCID 58124810, compound

Product 1

HCID 58124846HCID 58124846, compound

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

A solution of 200 μl of ethyloxalyl chloride in 1 ml of diethyl ether was added dropwise at 0° C. to a solution of 450 mg of 1c (contaminated with elimination products from previous reaction) and 200 μl of triethyl amine in 5 ml of ether. The reaction mixture was stirred for 20 min and then diluted with 10 ml of 1M K2CO3 and stirred for 5 min. The product was extracted with ethyl acetate and the extracts were washed once with water, dried and concentrated. The crude material was passed through a short silica column, using a gradient of heptane/ethyl acetate, as eluent, to provide 120 mg of 1d as colorless oil;

Workup

  1. stirringstirred for 5 min
  2. extractionThe product was extracted with ethyl acetate
  3. washthe extracts were washed once with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a847711aa6c6443ea905fbc3f2b305ad
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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