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

HRID 10199Notes

Reaction equation

HRID 10199 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-c7e7762d101746bb97da29c5d5af1395
Source dataset
uspto-grants-2006_08
Patent number
US07094778B2

Reaction notes

Loading…