Water → HCID 58124887, compound

HRID 1971668Notes

Reaction equation

HRID 1971668 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][CH2:7][S:8][CH2:9][C:10]#[C:11][C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)([CH3:4])[CH3:3].CC[C:19]([C:21](Cl)=[O:22])=[O:20].[OH2:24].[CH2:25](OCC)[CH3:26]>C(N(CC)CC)C>[C:2]([N:5]([CH2:6][CH2:7][S:8][CH2:9][C:10]#[C:11][C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[C:19](=[O:20])[C:21]([O:22][CH2:25][CH3:26])=[O:24])([CH3:1])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 11007880Butanoyl chloride, 2-oxo-HCID 58124796HCID 58124796, compound

Product 1

HCID 58124887HCID 58124887, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 1.63 of 9e in 20 ml of diethyl ether and 1.4 ml of triethyl amine was added, at 0° C., 0.8 ml of ethyloxalyl chloride. The reaction mixture was stirred for ½ h and then poured into water and extracted with ethyl acetate. The extract was washed with 1M aq. K2CO3 and water, dried and concentrated. The residue was chromatographed over silica gel, using a gradient of heptane/ethyl acetate as eluent, to provide 950 mg of 9f.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 1M aq. K2CO3 and water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-e28328888033427389797db934b8c60b
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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