m-Chloroperbenzoic acid → HCID 70055726, compound

HRID 1199738Notes

Reaction equation

HRID 1199738 reaction equation
[OH:1][C@H:2]1[C@@H:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH2:7][C:6]2[CH:17]=[C:18]([S:21][CH3:22])[CH:19]=[CH:20][C:5]=2[NH:4][C:3]1=[O:23].ClC1C=C(C=CC=1)C(OO)=[O:29]>C(Cl)Cl.C(OCC)(=O)C>[OH:1][C@H:2]1[C@@H:8]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[CH2:7][C:6]2[CH:17]=[C:18]([S:21]([CH3:22])=[O:29])[CH:19]=[CH:20][C:5]=2[NH:4][C:3]1=[O:23]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70361848HCID 70361848, compound

Product 1

HCID 70055726HCID 70055726, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of (cis)-1,3,4,5-Tetrahydro-3-hydroxy-7-methylthio-4-(4-methoxyphenyl)-2H-1-benzazepin-2-one (1.0 g, 3.04 mmol) in dry methylene chloride (30 ml) at 5° C. was treated with m-chloroperoxybenzoic acid (0.615 g, 3.04 mmol). After 30 minutes, the reaction was complete and the reaction mixture was diluted with ethyl acetate, washed with saturated sodium hydrogen carbonate, water, and brine. The organic layer was filtered and concentrated in vacuo to give a solid residue (1.02×g). Trituration with hot ethyl acetate, cooling and filtration afforded the product (600 mg), m.p. 214°14 216° C. The mother liquors were concentrated in vacuo and chromatographed on LPS-1 silica (methylene chloride/methanol). The product fractions were combined and concentrated in vacuo, and the residue crystallized from ethyl acetate to give an additional 200 mg of product.

Workup

  1. washwashed with saturated sodium hydrogen carbonate, water, and brine
  2. filtrationThe organic layer was filtered
  3. concentrationconcentrated in vacuo
  4. customto give a solid residue (1.02×g)
  5. filtrationfiltration

Sources & evidence

ORD record
ord-a7fa39f4afc9423bab178376cd9f03e6
Source dataset
uspto-grants-1990_02
Patent number
US04902684

Reaction notes

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