Ethyl bromoacetate → HCID 22393120, compound

HRID 458912Notes

Reaction equation

HRID 458912 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 overnight. 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 (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-0f41f597bc4347b588b62b3e5a58d78d
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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