Hydrochloric Acid → HCID 15752888, compound

HRID 1087593Notes

Reaction equation

HRID 1087593 reaction equation
[CH:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([OH:22])[C:8]([O:10][C:11]([CH3:21])([CH3:20])[C:12]#[C:13][CH2:14]N(CC)CC)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N#C[Br:31].O.Cl>C(OCC)C>[CH:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([OH:22])[C:8]([O:10][C:11]([CH3:21])([CH3:20])[C:12]#[C:13][CH2:14][Br:31])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10476Cyanogen BromideHCID 148166Temiverine

Product 1

HCID 15752888HCID 15752888, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 9.5 g 4-diethylamino-1,1-dimethyl-2-butynyl α-cyclohexyl-α-phenylglycolate in diethyl ether, was added dropwise an etheral solution of 3.2 g cyanogen bromide, and the mixture was stirred for one hour under ice cooling and then for 18 hours under cooling with water. 2N-HCl (14 ml) was added to the reaction mixture under ice cooling, and the separated etheral layer was collected, washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue left was purified by silica gel column chromatography (Wako Gel C-200; 1:15 mixture of ethyl acetate and n-hexane), giving 6.0 g of the objective compound as colorless oil.

Workup

  1. customthe separated etheral layer was collected
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. waitThe residue left
  6. customwas purified by silica gel column chromatography (Wako Gel C-200; 1:15 mixture of ethyl acetate and n-hexane)

Sources & evidence

ORD record
ord-6ceb53b0b9bd47c9b9e854ac9e8d3059
Source dataset
uspto-grants-1991_07
Patent number
US05036098

Reaction notes

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