Sodium Hydroxide → HCID 18442430, compound

HRID 458936Notes

Reaction equation

HRID 458936 reaction equation
[O:1]=[S:2]1(=[O:37])[C:8]2[CH:9]=[C:10]([O:15][CH2:16][C:17]([O:19]CC)=[O:18])[C:11]([S:13][CH3:14])=[CH:12][C:7]=2[N:6]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[CH2:5][C:4]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:3]1.[OH-].[Na+]>C(O)C>[O:37]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:15][CH2:16][C:17]([OH:19])=[O:18])[C:11]([S:13][CH3:14])=[CH:12][C:7]=2[N:6]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[CH2:5][C:4]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18442431HCID 18442431, compound

Product 1

HCID 18442430HCID 18442430, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1,1-dioxo-3,3-dibutyl-5-(4-chlorophenyl)-7-methylthio-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 100; 0.195 g, 0.343 mmol) in ethanol (8 ml) was added NaOH (1.03 mmol in 0.5 ml water). The reaction mixture was stirred at room temperature for 70 min and then quenched by adding acetic acid (0.3 ml). The solvent was evaporated under reduced pressure and the residue was extracted with DCM/water. The organic layer was separated, washed with brine, dried and evaporated under reduced pressure to give the title compound 0.169 g (91%). NMR (500 MHz, CD3OD) 0.86 (t, 6H), 1.11–1.28 (m, 8H), 1.37–1.44 (m, 4H), 2.33 (s, 3H), 3.25 (s, 2H), 3.55 (s, 2H), 4.73 (s, 2H), 7.10–7.15 (m, 3H), 7.26 (s, 1H), 7.28–7.32 (m, 2H).

Workup

  1. customquenched
  2. additionby adding acetic acid (0.3 ml)
  3. customThe solvent was evaporated under reduced pressure
  4. extractionthe residue was extracted with DCM/water
  5. customThe organic layer was separated
  6. washwashed with brine
  7. customdried
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-288cbbba2f134bd899bf4c363a07d3a0
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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