Hydrochloric Acid → HCID 17751371, compound

HRID 1641545Notes

Reaction equation

HRID 1641545 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]2([NH:32]C(=O)C)[CH2:29][O:28]C(C)(C)[O:26][CH2:25]2)=[CH:18][CH:17]=1.Cl>C(O)C>[NH2:32][C:24]([CH2:23][CH2:22][C:19]1[CH:18]=[CH:17][C:16]([C:3]2[CH:4]=[CH:5][C:6]([S:8][C:9]3[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=3)=[CH:7][C:2]=2[F:1])=[CH:21][CH:20]=1)([CH2:29][OH:28])[CH2:25][OH:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57624607HCID 57624607, compound

Product 1

HCID 17751371HCID 17751371, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

N-(5-{2-[2′-Fluoro-4′-(4-methylphenylthio)biphenyl-4-yl]ethyl}-2,2-dimethyl-1,3-dioxan-5-yl)acetamide (1.187 g) was dissolved in ethanol (20 mL), concentrated hydrochloric acid (10 mL) was added, and the mixture was stirred at 80° C. for 5 hr. The reaction mixture was concentrated, aqueous potassium carbonate solution was added to the residue, and the precipitated crystals were collected by filtration. The crude crystals were purified by preparative HPLC to give the title compound (491 mg) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionaqueous potassium carbonate solution was added to the residue
  3. filtrationthe precipitated crystals were collected by filtration
  4. customThe crude crystals were purified by preparative HPLC

Sources & evidence

ORD record
ord-7e4d1a8beb2641efb6fcff37875b263b
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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