Dichloromethane → 2-Bromo-4-ethoxycarbonyl(methanesulfonyloxy) methyl-1,7-di(trimethylsilylethoxymethyl)-6,7-dihydropyrrolo [2,3-c]azepin-8-one

HRID 53899Notes

Reaction equation

HRID 53899 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(Cl)Cl.[Br:9][C:10]1[N:33]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:13]2[C:14](=[O:32])[N:15]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16](=C=O)[CH:17]=[C:18](OCC)[C:12]=2[C:11]=1[CH2:42][OH:43].[C:44](=[O:47])([O-])[OH:45].[Na+].[CH2:49](N(CC)CC)[CH3:50]>>[Br:9][C:10]1[N:33]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:40])([CH3:41])[CH3:39])[C:13]2[C:14](=[O:32])[N:15]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:31])[CH3:30])[CH2:16][CH:17]=[C:18]([C:44]([O:45][CH2:49][CH3:50])=[O:47])[C:12]=2[C:11]=1[CH2:42][O:43][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86750712HCID 86750712, compound

Product 1

HCID 867507112-Bromo-4-ethoxycarbonyl(methanesulfonyloxy) methyl-1,7-di(trimethylsilylethoxymethyl)-6,7-dihydropyrrolo [2,3-c]azepin-8-oneYield 99%

Procedure

A 0.046 ml amount of methanesulfonyl chloride was dropwise added under ice cooling to a 5 ml methylene chloride solution of 295 mg of the compound (13) synthesized in Example 3 and 0.21 ml of triethylamine. The mixture was stirred at room temperature for 1 hour. A saturated aqueous solution of sodium hydrogen carbonate was added thereto and extraction was performed with methylene chloride. The extract was washed with saturated saline, dried, filtered, and concentrated under reduced pressure to obtain a residue which was then purified by silica gel column chromatography (hexane:ether=2:3) to obtain 331 mg of the above-referenced compound (15) (yield 99%).

Workup

  1. extractionextraction
  2. washThe extract was washed with saturated saline
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a residue which
  7. customwas then purified by silica gel column chromatography (hexane:ether=2:3)

Sources & evidence

ORD record
ord-4126f2ff2eb14cc2a8d6229d2b7af19a
Source dataset
uspto-grants-1997_04
Patent number
US05621099

Reaction notes

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