Methanesulfonic Acid → HCID 72784234, compound

HRID 1928891Notes

Reaction equation

HRID 1928891 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:25]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:24][CH2:23][CH2:22][C:21]([C:30]([NH:32][C:33]4[CH:38]=[CH:37][C:36]([S:39]([CH2:41][C:42]5[N:46]([CH2:47][CH2:48][CH3:49])[CH:45]=[N:44][CH:43]=5)=[O:40])=[CH:35][CH:34]=4)=[O:31])=[CH:20][C:19]=3[CH:50]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[CH3:51][S:52]([OH:55])(=[O:54])=[O:53]>C(OCC)(=O)C>[CH3:51][S:52]([OH:55])(=[O:54])=[O:53].[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:25]([CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:24][CH2:23][CH2:22][C:21]([C:30]([NH:32][C:33]4[CH:34]=[CH:35][C:36]([S:39]([CH2:41][C:42]5[N:46]([CH2:47][CH2:48][CH3:49])[CH:45]=[N:44][CH:43]=5)=[O:40])=[CH:37][CH:38]=4)=[O:31])=[CH:20][C:19]=3[CH:50]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 6320532HCID 6320532, compound

Product 1

HCID 72784234HCID 72784234, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (−)-8-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[[1-propyl-1H-imidazol-5-yl]methyl]sulfinyl]phenyl]-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxamide (100 mg) in ethyl acetate (4 ml) was added dropwise a solution of methanesulfonic acid (9.31 μl) in ethyl acetate (2 ml) with vigorous stirring, after which the mixture was stirred under light shielding overnight. The precipitated crystals were filtered, and further washed with ethyl acetate (5 ml), followed by drying under reduced pressure. The resulting crystals were recrystallized from 2-butanone (4 ml) to give (−)-8-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[[1-propyl-1H-imidazol-5-yl]methyl]sulfinyl]phenyl]-1,2,3,4-tetrahydro-1-benzoazocine-5-carboxamide methanesulfonate (88.4 mg) as yellow crystals (Compound 14).

Workup

  1. filtrationThe precipitated crystals were filtered
  2. washfurther washed with ethyl acetate (5 ml)
  3. customby drying under reduced pressure
  4. customThe resulting crystals were recrystallized from 2-butanone (4 ml)

Sources & evidence

ORD record
ord-5a6051cf31d341188a42c8c758f7645d
Source dataset
uspto-grants-2012_05
Patent number
US08183273B2

Reaction notes

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