Ethyl Acetate → HCID 131721070, compound

HRID 342500Notes

Reaction equation

HRID 342500 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19]SC2C=CC(OC)=CC=2)[NH:12][C:11]([CH2:29][C:30]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)=[O:31])=[C:10]1[C:39]([O:41][CH3:42])=[O:40].Cl[C:44]1[CH:45]=[C:46]([CH:51]=[CH:52][CH:53]=1)C(OO)=O.[OH:54][S:55]([O-:57])=O.[Na+].[OH-].[Na+].[C:61](OCC)(=[O:63])C>O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][S:55]([C:53]2[CH:44]=[CH:45][C:46]([O:63][CH3:61])=[CH:51][CH:52]=2)(=[O:57])=[O:54])[NH:12][C:11]([CH2:29][C:30]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)=[O:31])=[C:10]1[C:39]([O:41][CH3:42])=[O:40]

Participants

7

Reactant 5

HCID 8857Ethyl Acetate2×HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 23665763Sodium BisulfiteHCID 67624415HCID 67624415, compound

Product 1

HCID 131721070HCID 131721070, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of dimethyl 4-(2,6-dichlorophenyl)-6-(4-methoxyphenyl)thiomethyl-2-(4-methyl-1-piperazinyl)cabonylmethyl-1,4-dihydropyridine-3,5-dicarboxylate (1.01 g, 1.59 mmol) in ethyl acetate(15 ml) was added m-chloroperoxybenzoic acid (0.432 g, 2.07 mmol) in one portion at 0° C. and stirred for 10 min, then additional m-chloroperoxybenzoic acid (0.432 g, 2.07 mmol) was added and stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate (50 ml) and water (50 ml) followed by addition of NaHSO3 aqueous solution (260 mg included in water). After 10 min stirring, the pH was adjusted to 9.0 with NaOH solution. The organic layer separated was washed twice with water and brine, dried over Na2SO4, and concentrated to afford 795 mg of crude product. This was chromatographed on 50 g silica gel (dichloromethane/methanol: 22/3 as eluent) to yield 242 mg of title compound.

Workup

  1. stirringstirred at room temperature for 16 h
  2. stirringAfter 10 min stirring
  3. customThe organic layer separated
  4. washwas washed twice with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford 795 mg of crude product
  8. customThis was chromatographed on 50 g silica gel (dichloromethane/methanol: 22/3 as eluent)

Sources & evidence

ORD record
ord-60339b311df345189ee553442f4c1dc4
Source dataset
uspto-grants-1999_01
Patent number
US05859011

Reaction notes

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