Sodium methanethiolate → HCID 18442425, compound

HRID 458932Notes

Reaction equation

HRID 458932 reaction equation
[CH3:1][S-:2].[Na+].[O:4]=[S:5]1(=[O:35])[C:11]2[CH:12]=[C:13]([O:17][CH3:18])[C:14](Br)=[CH:15][C:10]=2[N:9]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[C:8](=[O:26])[C:7]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:6]1>CN(C=O)C>[O:4]=[S:5]1(=[O:35])[C:11]2[CH:12]=[C:13]([O:17][CH3:18])[C:14]([S:2][CH3:1])=[CH:15][C:10]=2[N:9]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[C:8](=[O:26])[C:7]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:6]1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 18442424HCID 18442424, compound

Product 1

HCID 18442425HCID 18442425, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium methanethiolate (0.43 g, 6.08 mmol) was added to a solution of 1,1-dioxo-3,3-dibutyl-4-oxo-5-(4-chlorophenyl)-7-bromo-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 96; 0.66 g, 1.22 mmol) in anhydrous DMF (11 ml) under nitrogen. The reaction mixture was stirred at room temperature for 72 hours. The solvent was evaporated under reduced pressure and the residue was extracted with trichloromethane/water. The organic layer was separated, washed with brine, dried and evaporated under reduced pressure. The crude product was purified by column chromatography using DCM as eluent to give the title compound 0.6 g (96%). NMR (500 MHz) 0.80–1.0 (m, 6H), 1.10–1.6 (m, 10H), 1.70–2.0 (m, 2H), 2.28 (s, 3H), 3.37–3.70 (m, 2H), 4.04 (s, 3H), 6.65 (s, 1H), 7.25–7.30 (m, 2H), 7.35–7.42 (m, 3H); m/z 510.4.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted with trichloromethane/water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-e541f018ef104de19759536392d3093d
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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