Sodium Hydroxide → HCID 21896699, compound

HRID 719101Notes

Reaction equation

HRID 719101 reaction equation
[O:1]=[S:2]1(=[O:35])[C:8]2[CH:9]=[C:10]([O:14][CH2:15][C:16]([O:18]CC)=[O:17])[C:11]([Br:13])=[CH:12][C:7]=2[N:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:5][C:4]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[NH:3]1.[OH-].[Na+]>CCO>[O:35]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:14][CH2:15][C:16]([OH:18])=[O:17])[C:11]([Br:13])=[CH:12][C:7]=2[N:6]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:5][C:4]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[NH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21896672HCID 21896672, compound

Product 1

HCID 21896699HCID 21896699, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1,1-dioxo-3,3-dibutyl-5-phenyl-7-bromo-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine (Method 1; 0.184 g, 3.24*10−4 mol) in EtOH (7 ml) was added NaOH (0.052 g, 1.30 mmol) and the mixture was stirred overnight. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and 0.5 M HCl. The aqueous layer was extracted twice more with EtOAc and the combined organic extracts were washed with brine and concentrated. The crude product was purified by preparative HPLC using an MeCN/ammonium acetate buffer as eluent and freeze-dried to give the title compound in 0.173 g (99%) as a white solid. NMR (400 MHz, CD3OD) 0.70–0.85 (m, 6H), 0.95–1.70 (m, 12H), 3.90 (brs, 2H), 4.50 (s, 2H), 6.90–7.40 (m, 7H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and 0.5 M HCl
  3. extractionThe aqueous layer was extracted twice more with EtOAc
  4. washthe combined organic extracts were washed with brine
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC
  7. customfreeze-dried

Sources & evidence

ORD record
ord-d04ee7f5fa0f457dbd47b1f5f6cf6b1a
Source dataset
uspto-grants-2006_11
Patent number
US07132416B2

Reaction notes

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