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Ethyl bromoacetate → HCID 18442482, compound

HRID 458945
Notes
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Reaction equation

HRID 458945 reaction equation
[O:1]=[S:2]1(=[O:26])[C:8]2[CH:9]=[C:10]([OH:13])[CH:11]=[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]=[C:10]([O:13][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:11]=[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 9864334HCID 9864334, compound

Product 1

HCID 18442482HCID 18442482, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalyst
HCID 6342
Acetonitrile
Solvent

Procedure

1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepin (WO9616051; 0.40 g, 1.07 mmol), ethyl bromoacetate (0.23 g, 1.38 mmol), sodium carbonate (0.50 g, 4.7 mmol) and tetrabutylammonium bromide (30 mg, 0.093 mmol) were added to MeCN (10 ml). The mixture was refluxed for 18 hours and then evaporated under reduced pressure. The residue was extracted with DCM/water. The DCM layer was separated and evaporated under reduced pressure. The residue was purified by column chromatography. The product was eluted with DCM/EtOAc (90:10). 0.480 g (97%) of the title compound was obtained. NMR (300 MHz) 0.7–0.85 (m, 6H), 1.0–1.7 (m, 11H), 3.1–3.3 (m, 2H), 3.6–3.8 (m, 2H), 4.3 (q, 2H), 4.6 (s, 2H), 6.9–7.3 (m, 7H), 7.5 (d, 1H).

Workup

  1. temperatureThe mixture was refluxed for 18 hours
  2. customevaporated under reduced pressure
  3. extractionThe residue was extracted with DCM/water
  4. customThe DCM layer was separated
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washThe product was eluted with DCM/EtOAc (90:10)

Sources & evidence

ORD record
ord-b41942572ad64d8f8405bcc59ddc7023
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07192945B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes