Ethyl bromoacetate → HCID 22393126, compound

HRID 1071299Notes

Reaction equation

HRID 1071299 reaction equation
[O:1]=[S:2]1(=[O:26])[C:8]2[CH:9]=[CH:10][C:11]([OH:13])=[CH:12][C:7]=2[N:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:5][C:4]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:20][CH3:21])[CH2:3]1.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])[O-].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC#N>[O:26]=[S:2]1(=[O:1])[C:8]2[CH:9]=[CH:10][C:11]([O:13][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:12][C:7]=2[N:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:5][C:4]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:20][CH3:21])[CH2:3]1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 22393124HCID 22393124, compound

Product 1

HCID 22393126HCID 22393126, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (WO 96/16051; 100 mg, 0.27 mmol), ethyl bromoacetate (50 mg, 0.30 mmol), sodium carbonate (100 mg, 0.94 mmol) and tetrabutylammonium bromide (10 mg 0.031 mmol) were added to MeCN (4 ml). The mixture was refluxed for 20 h and then evaporated under reduced pressure. The residue was purified by column chromatography on silica gel. The product was eluted with DCM: ethyl acetate (50:50). 120 mg (97%) of the title compound was obtained. NMR (300 MHz): 0.7-0.9 (m, 6H), 1.0-1.8 (m, 11H), 3.1-3.25 (m, 2H), 3.6-3.8 (m, 2H), 4.3 (q, 2H), 4.6 (s, 2H), 6.9-7.1 (m, 5H), 7.2-7.3 (m, 2H), 7.5 (d, 1H).

Workup

  1. temperatureThe mixture was refluxed for 20 h
  2. customevaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel
  4. washThe product was eluted with DCM: ethyl acetate (50:50)

Sources & evidence

ORD record
ord-093dd8bd910949d6bedfdff4fc6d6ba5
Source dataset
uspto-grants-2005_06
Patent number
US06906058B2

Reaction notes

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