m-Chloroperbenzoic acid → HCID 13885779, compound

HRID 580012Notes

Reaction equation

HRID 580012 reaction equation
[CH:1]([O:4][C:5]1[N:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]([F:37])([F:36])[F:35])[C:8]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:9]([CH2:15][S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:10]2)([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:43].C(=O)([O-])O.[Na+]>ClCCl>[CH:1]([O:4][C:5]1[N:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]([F:35])([F:36])[F:37])[C:8]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:9]([CH2:15][S:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:43])[NH:10]2)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 13885770HCID 13885770, compound

Product 1

HCID 13885779HCID 13885779, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g (1.9 mMole) ethyl (±)-1,4-dihydro-5-isopropoxy-2-phenylthiomethyl-4-(2-trifluoromethylphenyl)-1,6-naphthyridine-3-carboxylate (Example 3.d) in 30 ml dichloromethane is cooled to 0° C. and 0.4 g (2.1 mMole) 3-chloroperoxy-benzoic acid (90%) is added portionwise thereto. After 10 minutes at 0° C., an aqueous solution of sodium hydrogen carbonate is added dropwise thereto and the organic phase is separated off, washed with water and dried over anhydrous sodium sulphate. After distilling off the solvent, the residue obtained is recrystallized from ethyl acetate. There is obtained ethyl (±)-1,4-dihydro-5-isopropoxy-2-phenylsulphinylmethyl-4-(2-trifluoromethylphenyl)-1,6-naphthyridine-3-carboxylate in the form of colorless crystals; mp 206°-208° C.

Workup

  1. customthe organic phase is separated off
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. distillationAfter distilling off the solvent
  5. customthe residue obtained
  6. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3ef7b0a030e548a891b7f8e5d7d6a9a6
Source dataset
uspto-grants-1988_06
Patent number
US04751228

Reaction notes

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