Hydrochloric Acid → HCID 69545788, compound

HRID 2086297Notes

Reaction equation

HRID 2086297 reaction equation
C(OC([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[C:10]1=[O:27])=O)(C)(C)C.Cl.[CH3:29][O:30][C:31]1[CH:40]=[C:39]2[C:34]([CH:35]=[CH:36][C:37]([S:41](Cl)(=[O:43])=[O:42])=[CH:38]2)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO.C(OCC)(=O)C.C(N(CC)CC)C.ClCCl>[CH3:29][O:30][C:31]1[CH:40]=[C:39]2[C:34]([CH:35]=[CH:36][C:37]([S:41]([NH:8][C@H:9]3[CH2:13][CH2:12][N:11]([NH:14][CH:15]4[CH2:16][CH2:17][N:18]([C:21]5[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=5)[CH2:19][CH2:20]4)[C:10]3=[O:27])(=[O:43])=[O:42])=[CH:38]2)=[CH:33][CH:32]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 105152667-methoxynaphthalene-2-sulfonyl ChlorideHCID 69545831HCID 69545831, compound

Product 1

HCID 69545788HCID 69545788, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3S)-3-(tert-butoxycarbonylamino)-1-[1-(4-pyridyl)-4-piperidinylamino]-2-pyrrolidone (220 mg) in methanol (10 ml) was combined with a 4N solution of hydrochloric acid in ethyl acetate (10 ml) and stirred at room temperature for 30 minutes. The reaction mixture was concentrated and the residue obtained was combined with dichloromethane (20 ml) and triethylamine (700 ml), followed by 7-methoxynaphthalene-2-sulfonyl chloride (150 ml) at 0° C., and then stirred at room temperature for 1 hour. The reaction mixture was combined with an aqueous solution of sodium carbonate, extracted with dichloromethane, dried, concentrated and purified by a column chromatography dichloromethane: 10% aqueous ammonia-containing methanol=20:1) to obtain the title compound (123 mg) as a colorless amorphous material.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue obtained
  3. stirringstirred at room temperature for 1 hour
  4. extractionextracted with dichloromethane
  5. customdried
  6. concentrationconcentrated
  7. custompurified by a column chromatography dichloromethane
  8. addition10% aqueous ammonia-containing methanol=20:1)

Sources & evidence

ORD record
ord-9093d822023f4eac817529dd88c436f1
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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