Hydrochloric Acid → HCID 46202559, compound

HRID 1641566Notes

Reaction equation

HRID 1641566 reaction equation
C([O:4][CH2:5][C:6]([NH:36]C(=O)C)([CH2:31][O:32]C(=O)C)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([S:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)=[CH:17][C:16]=2[F:29])=[CH:11][C:10]=1[Cl:30])(=O)C.Cl>C(O)C>[NH2:36][C:6]([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([S:21][C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)=[CH:17][C:16]=2[F:29])=[CH:11][C:10]=1[Cl:30])([CH2:31][OH:32])[CH2:5][OH:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57624589HCID 57624589, compound

Product 1

HCID 46202559HCID 46202559, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

N-[1,1-Bis(acetoxymethyl)-3-[3-chloro-2′-fluoro-4′-(4-methylphenylthio)biphenyl-4-yl]propyl]acetamide (0.24 g) was dissolved in ethanol (4 mL), concentrated hydrochloric acid (2 mL) was added, and the mixture was stirred at 75° C. for 3 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 (106 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-c117c61e4da1491ea7414b8c1dfde8f9
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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