Methanesulfonic Acid → HCID 72784234, compound

HRID 2222783Notes

Reaction equation

HRID 2222783 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-benzazocine-5-carboxamide (100 mg) in ethyl acetate (4 ml) was added dropwise to 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-1benzazocine-5-carboxamide methansulfonate (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-a7b19493c0774e878408abed11411eca
Source dataset
uspto-grants-2008_05
Patent number
US07371772B2

Reaction notes

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