Water → HCID 68835518, compound

HRID 1784410Notes

Reaction equation

HRID 1784410 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][C:13]([S:18][C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)([N:15]([CH3:17])[CH3:16])[C:12]2[CH:26]=[CH:27][CH:28]=[CH:29][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH2:30].[OH2:31].O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=O.[Mg+2].S([O-])([O-])=O.[Na+].[Na+].O>ClCCl.CO>[CH3:3][C:1]([O:5][C:6]([N:8]1[CH2:14][C:13]([S:18]([C:19]2[CH:20]=[CH:21][C:22]([Br:25])=[CH:23][CH:24]=2)(=[O:31])=[O:30])([N:15]([CH3:17])[CH3:16])[C:12]2[CH:26]=[CH:27][CH:28]=[CH:29][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)2×HCID 68833330HCID 68833330, compound

Product 1

HCID 68835518HCID 68835518, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

(4-Bromo-phenylsulfanyl)-dimethylamino-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester (2.8 g, 6.0 mmol) in dichloromethane (5 ml) was added to magnesium monoperoxyphthalate hexahydrate (MMPP) (7.4 g, 80%) in dichloromethane (20 ml) and methanol (3 ml) at 0° C. dropwise. After addition the mixture was allowed to warm to room temperature and stirred for 1 h then a further portion of MMPP (1 g) was added and stirred for a further 1 h. Sodium sulfite solution (10%, 300 ml) was added and the mixture stirred thoroughly for 30 min). Water (3 L) and dichloromethane (400 ml) were then added and the organic layer separated and washed with sodium bicarbonate solution (500 ml), water (2×1 L) and brine (500 ml) then evaporated in vacuo. Chromatography on silica eluting with 0-20% ethyl acetate/hexane afforded 3.22 g of the subtitled compound. MH+ 510.

Workup

  1. additionAfter addition the mixture
  2. stirringstirred for a further 1 h
  3. stirringthe mixture stirred thoroughly for 30 min)
  4. customthe organic layer separated
  5. washwashed with sodium bicarbonate solution (500 ml), water (2×1 L) and brine (500 ml)
  6. customthen evaporated in vacuo

Sources & evidence

ORD record
ord-cd0eaf6558a54fb7946bd90212aa4f02
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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