Ethyl bromoacetate → HCID 22393120, compound

HRID 1071308Notes

Reaction equation

HRID 1071308 reaction equation
[O:1]=[S:2]1(=[O:28])[C:8]2[CH:9]=[C:10]([OH:15])[C:11]([O:13][CH3:14])=[CH:12][C:7]=2[N:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5][C:4]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:22][CH3:23])[CH2:3]1.Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(=O)([O-])[O-].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC#N>[O:28]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:15][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:11]([O:13][CH3:14])=[CH:12][C:7]=2[N:6]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:5][C:4]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:22][CH3:23])[CH2:3]1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 22393106HCID 22393106, compound

Product 1

HCID 22393120HCID 22393120, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

1,1-dioxo-3-butyl-3-ethyl-5-phenyl-7-methoxy-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (WO 9616051; 1.0 g), ethyl bromoacetate (0,50 g), sodium carbonate (1.2 g) and tetrabutylammonium bromide (60 mg) in MeCN (15 ml) were refluxed over night. The solvent was removed under reduced pressure and the residue was extracted (DCM/H2O). The organic layer was separated and the solvent was removed under reduced pressure. The residue purified by chromatography (DCM/EtOAc (90:10)) to give the title compound 1.2 g (98%). NMR (400 MHz, CD3OD) 0.75-0.85 (m, 6H), 1.00-1.30 (m, 8H), 1.35-1.55 (m, 4H), 3.20 (s, 2H), 3.65 (s, 3H), 3.70 (brs, 2H), 4.50 (s, 2H), 6.50 (s, 1H), 6.90-7.30 (m,5H), 7.40 (s, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe residue was extracted (DCM/H2O)
  3. customThe organic layer was separated
  4. customthe solvent was removed under reduced pressure
  5. customThe residue purified by chromatography (DCM/EtOAc (90:10))

Sources & evidence

ORD record
ord-8334473c334346578a9854a53a46afeb
Source dataset
uspto-grants-2005_06
Patent number
US06906058B2

Reaction notes

Loading…