Acetic Acid → HCID 18442481, compound

HRID 458944Notes

Reaction equation

HRID 458944 reaction equation
[O:1]=[S:2]1(=[O:32])[C:8]2[CH:9]=[C:10]([O:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH:11]=[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)(=O)C>C(O)C>[O:32]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:13][CH2:14][C:15]([OH:17])=[O:16])[CH:11]=[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 176Acetic AcidHCID 14798Sodium HydroxideHCID 18442482HCID 18442482, compound

Product 1

HCID 18442481HCID 18442481, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 116; 0.48 g, 1.04 mmol) was dissolved in ethanol (10 ml). NaOH (0.30 g, 7.5 mmol) was added and the mixture was refluxed for 30 min. Acetic acid (1 ml) was added. The solvent was evaporated under reduced pressure and the residue was extracted with DCM/water. The DCM layer was separated, dried and evaporated. 0.44 g (97%) of the title compound was obtained. NMR (300 MHz) 0.7–0.8 (m, 6H), 1.0–1.6 (m, 8H), 3.1–3.3 (m, 2H), 3.5–3.8 (m, 2H), 4.6 (s, 3H), 6.8–7.3 (m, 7H), 7.5 (s, 1H).

Workup

  1. temperaturethe mixture was refluxed for 30 min
  2. customThe solvent was evaporated under reduced pressure
  3. extractionthe residue was extracted with DCM/water
  4. customThe DCM layer was separated
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-03271c407e504e408798d438b2bf8f51
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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