Sulfuric acid magnesium salt (1:1) → HCID 131724408, compound

HRID 2085651Notes

Reaction equation

HRID 2085651 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][N:11]([CH2:19][CH2:20][S:21][CH3:22])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][C:3]=1[C:23]([NH:25][CH2:26][C:27]12[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[CH2:28]1)[CH2:34]2)=[O:24].ClC1C=C(C=CC=1)C(OO)=[O:42].[OH-].[Ca+2].[OH-].S([O-])([O-])(=O)=O.[Mg+2]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][N:11]([CH2:19][CH2:20][S:21]([CH3:22])=[O:42])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][C:3]=1[C:23]([NH:25][CH2:26][C:27]12[CH2:28][CH:29]3[CH2:35][CH:33]([CH2:32][CH:31]([CH2:30]3)[CH2:36]1)[CH2:34]2)=[O:24]

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 131724407HCID 131724407, compound

Product 1

HCID 131724408HCID 131724408, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared according to the method of Example 22 from [2-[[4-chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]amino]ethyl][2-(methylthio)ethyl]-carbamic acid, 1,1-dimethylethyl ester (0.460 g, Example 30a), 3-chloroperoxybenzoic acid (0.315 g) and dichloromethane (20 ml). Excess calcium hydroxide was added, followed by excess magnesium sulfate. The mixture was filtered through celite and concentrated under reduced pressure. The crude material was purified on silica gel (19:1/dichloromethane:methanol) to afford the sub-title compound as a gum (0.141 g) and the corresponding sulfone (0.057 g).

Workup

  1. customPrepared
  2. filtrationThe mixture was filtered through celite and
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified on silica gel (19:1/dichloromethane:methanol)

Sources & evidence

ORD record
ord-2286d9230913487eb2549a7321230a88
Source dataset
uspto-grants-2004_04
Patent number
US06720452B2

Reaction notes

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