Acetyl chloride → HCID 10178010, compound

HRID 393173Notes

Reaction equation

HRID 393173 reaction equation
[H-].[K+].[C:3]1([CH:13]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][N:17]3[C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[S:14]2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[C:28](Cl)(=[O:30])[CH3:29]>C1COCC1>[C:28]([O:20][C:19]1[C:18]2=[CH:21][CH:22]=[CH:23][N:17]2[C:16]2[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=2[S:14][C:13]=1[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 82127Potassium hydrideHCID 11152016HCID 11152016, compound

Product 1

HCID 10178010HCID 10178010, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of potassium hydride (0.303 g, 2.64 mmol, 35% in oil) in anhydrous THF (5.0 mL) was added the (±)-6-(1-naphthyl)pyrrolo[2,1-d][1,5]benzothiazepin-7(6H)-one (0.9 g, 2.64 mmol) dissolved in anhydrous THF (7 mL). The reaction mixture was stirred at rt for 2 h, and then acetyl chloride (0.239 g, 3.04 mmol) was slowly added. After stirring for 12 h at rt, the solvent was removed in vacuo and the residue was dissolved in chloroform. The organic layer was washed with brine, dried and concentrated. The residue was chromatographed (dichloromethane and hexane 1:1) to give the PBOX-9 in 86% yield. IR (neat) 1762 cm−1; 1HNMR (CDCl3) δ 1.70 (s, 3 H) 6.45 (m, 1 H), 6.63 (m, 1 H), 7.19-7.55 (m, 10 H), 7.78-7.87 (m, 2 H).

Workup

  1. stirringAfter stirring for 12 h at rt
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed (dichloromethane and hexane 1:1)
  8. customto give the PBOX-9 in 86% yield

Sources & evidence

ORD record
ord-50922b1ecac148deb8a37db9074ff6d8
Source dataset
uspto-grants-2004_10
Patent number
US06806267B1

Reaction notes

Loading…