Cesium carbonate → HCID 18442470, compound

HRID 458926Notes

Reaction equation

HRID 458926 reaction equation
[O:1]=[S:2]1(=[O:28])[C:8]2[CH:9]=[C:10]([O:14][CH3:15])[C:11](Br)=[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.C([O-])([O-])=O.[Cs+].[Cs+].[C:35]([O:39]CC)(=[O:38])[CH2:36][SH:37]>CN(C=O)C.O>[O:1]=[S:2]1(=[O:28])[C:8]2[CH:9]=[C:10]([O:14][CH3:15])[C:11]([S:37][CH2:36][C:35]([OH:39])=[O:38])=[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

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 12185Ethyl ThioglycolateHCID 22393116HCID 22393116, compound

Product 1

HCID 18442470HCID 18442470, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-7-bromo-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (113 mg, 0.24 mmol), Cs2CO3 (170 mg, 0.52 mmol) and ethyl thioglycolate (0.060 ml, 0.54 mmol) in DMF (4.0 ml) were subjected to microwave irradiation in a Smith Synthesiser at 80° C. for 3 min and then at 90° C. for 8 min. The reaction mixture was diluted with water (250 ml) and extracted with DCM (5×10 ml) and collected organic layers were dried (MgSO4), concentrated and purified on a short column (petroleum ether: EtOAc 4:1→2:1). The resulting product was dissolved in THF (2 ml) and water (2 ml) and NaOH (aq., 0.5 ml, 1 M) was added and the reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched with HCl (1 M) and the reaction mixture was diluted with water (10 ml) and extracted with DCM (3×3 ml). Purification with preparative HPLC yielded the title compound (58 mg, 59%). NMR (300 MHz, CD3OD) 0.81 (m, 6H), 1.00–1.70 (m, 8H), 3.21 (m, 2H), 3.42 (m, 2H), 3.71 (m, 2H), 3.92 (s, 3H), 6.88 (m, 2H), 7.02 (m, 2H), 7.23 (t, 2H), 7.40 (s, 1H).

Workup

  1. customirradiation in a Smith Synthesiser at 80° C. for 3 min
  2. extractionextracted with DCM (5×10 ml)
  3. customcollected organic layers
  4. dry with materialwere dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified on a short column (petroleum ether: EtOAc 4:1→2:1)
  7. dissolutionThe resulting product was dissolved in THF (2 ml)
  8. additionwater (2 ml) and NaOH (aq., 0.5 ml, 1 M) was added
  9. customThe reaction was quenched with HCl (1 M)
  10. additionthe reaction mixture was diluted with water (10 ml)
  11. extractionextracted with DCM (3×3 ml)
  12. customPurification with preparative HPLC

Sources & evidence

ORD record
ord-9cc6dbd62ed34b109d2f32cb15c98b0d
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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