Hydrochloric Acid → HCID 69550750, compound

HRID 2214810Notes

Reaction equation

HRID 2214810 reaction equation
I[Si](C)(C)C.C(OC([NH:16][C:17]1([CH2:29][N:30]2[CH2:35][CH2:34][N:33]([S:36]([C:39]3[CH:48]=[CH:47][C:46]4[C:41](=[CH:42][CH:43]=[C:44]([Cl:49])[CH:45]=4)[CH:40]=3)(=[O:38])=[O:37])[CH2:32][C:31]2=[O:50])[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)=O)C1C=CC=CC=1.CO.[ClH:53]>ClCCl.C(OCC)(=O)C>[ClH:49].[ClH:53].[NH2:16][C:17]1([CH2:29][N:30]2[CH2:35][CH2:34][N:33]([S:36]([C:39]3[CH:48]=[CH:47][C:46]4[C:41](=[CH:42][CH:43]=[C:44]([Cl:49])[CH:45]=4)[CH:40]=3)(=[O:37])=[O:38])[CH2:32][C:31]2=[O:50])[CH2:22][CH2:21][N:20]([C:23]2[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=2)[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 85247Trimethylsilyl iodideHCID 69550015HCID 69550015, compound

Product 1

HCID 69550750HCID 69550750, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Iodotrimethylsilane (2.51 ml) was added to a solution of 1-[4-benzyloxycarbonylamino-1-(4-pyridyl)-4-piperidylmethyl]-4-(6-chloronaphthalene-2-sulfonyl)-2-piperazinone (4.58 g) in dichloromethane (50 ml), and the mixture was stirred at room temperature for 4 hours. Methanol (10 ml) and 4N hydrochloric acid solution in ethyl acetate (8 ml) were added thereto. Methanol was added to obtain a solution, followed by concentration under reduced pressure. Dilute hydrochloric acid was added to the residue, and the mixture was washed with ether. The aqueous layer was made basic with 6N sodium hydroxide, followed by extraction with ethyl acetate. The organic layer was washed successively with an aqueous sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried, and concentrated. Dilute hydrochloric solution was added to the residue, which was purified by CHP20 column chromatography (water:acetonitrile:1N hydrochloric acid=100:0:1→80:20:1) to obtain the colorless amorphous title compound (3.66 g).

Workup

  1. customto obtain a solution
  2. concentrationfollowed by concentration under reduced pressure
  3. additionDilute hydrochloric acid was added to the residue
  4. washthe mixture was washed with ether
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed successively with an aqueous sodium bicarbonate solution
  7. dry with materialan aqueous saturated sodium chloride solution, dried
  8. concentrationconcentrated
  9. additionDilute hydrochloric solution
  10. additionwas added to the residue, which
  11. customwas purified by CHP20 column chromatography (water:acetonitrile:1N hydrochloric acid=100:0:1→80:20:1)

Sources & evidence

ORD record
ord-b4d79b17acc44b0a81147ae01c2355ae
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

Loading…