Ammonium Chloride → HCID 9883124, compound

HRID 1107850Notes

Reaction equation

HRID 1107850 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[C:9](OC(C)(C)C)=O)#[N:2].[F:16][C:17]1[CH:22]=[CH:21][C:20]([Mg]Br)=[CH:19][CH:18]=1.[Cl-].[NH4+]>C(OCC)C>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:9]2[NH:2][C:1]([C:20]3[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=3)=[C:3]3[C:4]=2[CH2:5][CH2:6][CH2:7][CH2:8]3)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 54006118HCID 54006118, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 9883124HCID 9883124, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 14.75 g of the compound of Step A diluted with 30 ml of ethyl ether is added dropwise, at 35° C., to 80 ml of a 2M solution of 4-fluorophenylmagnesium bromide in ethyl ether. After 2 hours, the reaction mixture is cooled and hydrolysed with 20 ml of a saturated ammonium chloride solution. After filtration and washing with ethyl ether, the organic phases are combined and dried over calcium sulphate and then concentrated. The product is isolated by chromatography on silica gel (eluant: cyclohexane/ethyl acetate:97.5/2.5). Crystallisation yields 2 g of the product.

Workup

  1. filtrationAfter filtration
  2. washwashing with ethyl ether
  3. dry with materialdried over calcium sulphate
  4. concentrationconcentrated
  5. customThe product is isolated by chromatography on silica gel (eluant: cyclohexane/ethyl acetate:97.5/2.5)
  6. customCrystallisation

Sources & evidence

ORD record
ord-15cf77196aeb416ea3185dd024dbb271
Source dataset
uspto-grants-2000_05
Patent number
US06063804

Reaction notes

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