Hydrochloric Acid → 1-(4-{[(S)-2-(-4-methanesulfonyl-phenyl)-1-methylethyl]propylamino}butyl)-[1,4]diazepan-2-one, dihydrochloride salt

HRID 433089Notes

Reaction equation

HRID 433089 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]([C@@H:23]([CH3:35])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)[CH2:20][CH2:21][CH3:22])[C:10](=[O:36])[CH2:9]1)=O)(C)(C)C.[ClH:37].C(=O)([O-])[O-].[Na+].[Na+]>>[ClH:37].[ClH:37].[CH3:34][S:31]([C:28]1[CH:29]=[CH:30][C:25]([CH2:24][C@@H:23]([N:19]([CH2:20][CH2:21][CH3:22])[CH2:18][CH2:17][CH2:16][CH2:15][N:11]2[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][C:10]2=[O:36])[CH3:35])=[CH:26][CH:27]=1)(=[O:32])=[O:33]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 692253654-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methylethyl]propylamino}butyl)-3-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 1317242621-(4-{[(S)-2-(-4-methanesulfonyl-phenyl)-1-methylethyl]propylamino}butyl)-[1,4]diazepan-2-one, dihydrochloride salt

Conditions

Temperature
50 °C

Procedure

A mixture of 4-(4-{[(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]-propylamino}butyl)-3-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.9 g, 1.75 mmole) and 3N hydrochloric acid (4 mL) was warmed to 50° C. The reaction mixture was stirred at room temperature for 30 minutes, and the pH was adjusted to 10 with saturated sodium carbonate. The mixture was extracted with ethyl acetate (30 mL), and the organic phase was dried (magnesium sulfate), and concentrated. The residue was dissolved in diethyl ether (10 mL) and 1 M hydrogen chloride in diethyl ether (2 mL) was added. The precipitate was collected, washed with diethyl ether and hexane, and dried in vacuo to give 1-(4-{[(S)-2-(-4-methanesulfonyl-phenyl)-1-methylethyl]propylamino}butyl)-[1,4]diazepan-2-one, dihydrochloride salt (0.49 g),149, M+H=424.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (30 mL)
  2. dry with materialthe organic phase was dried (magnesium sulfate)
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in diethyl ether (10 mL)
  5. addition1 M hydrogen chloride in diethyl ether (2 mL) was added
  6. customThe precipitate was collected
  7. washwashed with diethyl ether and hexane
  8. customdried in vacuo

Sources & evidence

ORD record
ord-5513f3d5334b436ebe6217fd18888082
Source dataset
uspto-grants-2003_12
Patent number
US06667301B2

Reaction notes

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