Hydrochloric Acid → HCID 19095679, compound

HRID 486648Notes

Reaction equation

HRID 486648 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=3[Cl:30])=[C:19]([O:31][CH2:32][CH2:33][S:34][CH3:35])[N:18]=[C:17]([CH2:36][CH3:37])[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C[OH:40]>[OH-].[Na+].O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=3[Cl:30])=[C:19]([O:31][CH2:32][CH2:33][S:34]([CH3:35])=[O:40])[N:18]=[C:17]([CH2:36][CH3:37])[N:16]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 19095640HCID 19095640, compound

Product 1

HCID 19095679HCID 19095679, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

210 mg of 4-tert-butyl-N-[5-(2-chloro-5-methoxyphenoxy)-2-ethyl-6-(2-methylsulphanyl-ethoxy)-pyrimidin-4-yl]-benzenesulfonamide were dissolved in 5 ml of MeOH and 0.2 ml of 1N NaOH. 95 mg of NalO4 dissolved in 0.5 ml of H2O were added thereto and the mixture was stirred at room temperature for 5 hours, whereby a suspension resulted. Then, 0.2 ml of 1N HCl was added and the mixture was subsequently evaporated to dryness. The residue was partitioned between ethyl acetate and 0.1N HCl and worked-up as usual. For purification, the compound was chromatographed on silica gel using ethyl acetate-MeOH (6:1 by vol.) as the eluent. There were obtained 160 mg of (RS)-4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-2-ethyl-6-(2-methylsulphinyl-ethoxy)pyrimidin-4-yl]-benzenesulfonamide as a white powder. MS: 581 (M).

Workup

  1. additionwere added
  2. customwhereby a suspension resulted
  3. customthe mixture was subsequently evaporated to dryness
  4. customThe residue was partitioned between ethyl acetate and 0.1N HCl
  5. customFor purification
  6. customthe compound was chromatographed on silica gel

Sources & evidence

ORD record
ord-b0faa072379f450fbdba277095f04a33
Source dataset
uspto-grants-1994_03
Patent number
US05292740

Reaction notes

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