Ethyl bromoacetate → HCID 22393105, compound

HRID 458910Notes

Reaction equation

HRID 458910 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C([O-])([O-])=O.[Na+].[Na+].[O:14]=[S:15]1(=[O:43])[C:21]2[CH:22]=[C:23]([OH:28])[C:24]([O:26][CH3:27])=[CH:25][C:20]=2[N:19]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:18][C:17]([CH2:39][CH2:40][CH2:41][CH3:42])([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:16]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC#N>[O:43]=[S:15]1(=[O:14])[C:21]2[CH:22]=[C:23]([O:28][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:24]([O:26][CH3:27])=[CH:25][C:20]=2[N:19]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:18][C:17]([CH2:39][CH2:40][CH2:41][CH3:42])([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:16]1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 22393134HCID 22393134, compound

Product 1

HCID 22393105HCID 22393105, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

Ethyl bromoacetate (0.13 ml), Na2CO3 (0.40 g) and tetrabutylammonium bromide (0.030 g) were added to a solution of 1,1-dioxo-3,3-dibutyl-5-phenyl-7-methoxy-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (synthesised by the of WO9616051 for the corresponding 3-butyl-3-ethyl analogue; 0.400 g, 0.927 mmol) in MeCN (10 ml). The suspension was heated under reflux overnight before most of the solvent was removed under reduced pressure. The crude product was extracted (DCM/H2O) and filtered through a short silica-column (DCM:EtOAc-1:4) to give the title compound 0.476 g (99%). NMR 0.65–0.85 (m, 6H), 0.95–1.65 (m, 8H), 3.00–3.15 (m, 2H), 3.50–3.80 (m, 2H), 3.70–3.80 (s, 3H), 5.60 (s, 1H), 5.65 (d, 1H) 7.00–7.60 (m, 17H), 8.05–8.20 (d, 1H).

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux overnight before most of the solvent
  3. customwas removed under reduced pressure
  4. extractionThe crude product was extracted (DCM/H2O)
  5. filtrationfiltered through a short silica-column (DCM:EtOAc-1:4)

Sources & evidence

ORD record
ord-9f4a16ae1a3c42eab7f4267e008346df
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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