Ethanol → HCID 18442469, compound

HRID 1071298Notes

Reaction equation

HRID 1071298 reaction equation
[O:1]=[S:2]1(=[O:32])[C:8]2[CH:9]=[CH:10][C:11]([O:13][CH2:14][C:15]([O:17]CC)=[O:16])=[CH:12][C:7]=2[N:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:5][C:4]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:26][CH3:27])[CH2:3]1.[OH-].[Na+].C(O)C>CC(O)=O>[O:32]=[S:2]1(=[O:1])[C:8]2[CH:9]=[CH:10][C:11]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:12][C:7]=2[N:6]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:5][C:4]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:26][CH3:27])[CH2:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 22393126HCID 22393126, compound

Product 1

HCID 18442469HCID 18442469, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-(ethoxycarbonylmethoxy)-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 3; 110 mg, 0.24 mmol) and sodium hydroxide (100 mg, 2.5 mmol) were added to ethanol (5 ml, 95%). The mixture was refluxed for 1 h. AcOH (0.30 ml) was added and the reaction mixture was evaporated under reduced pressure. The residue was extracted with DCM/water. The DCM layer was separated, dried and evaporated under reduced pressure. The residue crystallised when treated with hexane. 82 mg (79%) of the title compound was obtained. NMR (500 MHz): 0.7-0.9 (m, 6H), 1.1-1.7 (m, 8H), 3.1-3.25 (m, 2H), 3.6-3.8 (br d, 2H), 4.6 (s, 2H), 6.9-7.1 (m, 5H), 7.2-7.3 (m, 2H),

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. customthe reaction mixture was evaporated under reduced pressure
  3. extractionThe residue was extracted with DCM/water
  4. customThe DCM layer was separated
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue crystallised when
  8. additiontreated with hexane

Sources & evidence

ORD record
ord-b9b4f19892ad4634a1dea07dc58322a7
Source dataset
uspto-grants-2005_06
Patent number
US06906058B2

Reaction notes

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