Acetic Acid → 1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-[1'-carboxyethoxy]-2,3,4,5-tetrahydro-1,5-benzothiazepine

HRID 458907Notes

Reaction equation

HRID 458907 reaction equation
[OH-].[Na+].[O:3]=[S:4]1(=[O:36])[C:10]2[CH:11]=[C:12]([O:16][CH:17]([C:19]([O:21]CC)=[O:20])[CH3:18])[C:13]([Br:15])=[CH:14][C:9]=2[N:8]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:7][C:6]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:30][CH3:31])[CH2:5]1.CC(O)=O>CCO>[O:36]=[S:4]1(=[O:3])[C:10]2[CH:11]=[C:12]([O:16][CH:17]([C:19]([OH:21])=[O:20])[CH3:18])[C:13]([Br:15])=[CH:14][C:9]=2[N:8]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:7][C:6]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:30][CH3:31])[CH2:5]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 223931141,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-(1-ethoxycarbonylethoxy)-2,3,4,5-tetrahydro-1,5-benzothiazepine

Product 1

HCID 223931111,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-[1'-carboxyethoxy]-2,3,4,5-tetrahydro-1,5-benzothiazepineYield 65.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide (0.045 g, 1.13 mmol) was added to a solution of 1,1-dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-[1-(ethoxycarbonyl)ethoxy]-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 1; 0.050 g, 0.090 mmol) in EtOH (4 ml, 95%) and heated under reflux. After 1.5 hours AcOH (0.2 ml) was added and most of the solvent was removed under reduced pressure. The crude product was extracted (DCM/H2O), dried (MgSO4) and evaporated to give the title compound 0.031 g (65%) as white solid. NMR (500 MHz, CD3OD) 0.70–0.85 (m, 6H), 0.95–1.25 (m, 4H), 1.35–1.70 (m, 4H), 2.65 (d, 3H), 3.10–3.35 (m, 2H), 3.45–3.95 (m, 2H), 4.70 (q, 1H), 6.90–7.35 (m, 6H), 7.45 (s, 1H).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customwas removed under reduced pressure
  4. extractionThe crude product was extracted (DCM/H2O)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-f0b4faa21906434eae449cc5a351f938
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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