Methanesulfonic Acid → HCID 10113998, compound

HRID 1744170Notes

Reaction equation

HRID 1744170 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([N:27]4[CH2:37][C@@H:36]([CH3:38])[CH2:35][C@H:28]4[C:29]([NH:31][CH2:32][C:33]#[N:34])=[O:30])[CH:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.CS(O)(=O)=O.C([O-])(O)=O.[Na+]>>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]2[CH:16]=[CH:15][C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:19][CH:18]=2)=[CH:21][C:22]=1[N:27]1[CH2:37][C@@H:36]([CH3:38])[CH2:35][C@H:28]1[C:29]([NH:31][CH2:32][C:33]#[N:34])=[O:30]

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 86594585HCID 86594585, compound

Product 1

HCID 10113998HCID 10113998, compound

Procedure

To (4S)-1-{4′-[4-(tert-butoxycarbonyl)piperazin-1-yl]-4-chloro-1,1′-biphenyl-3-yl}-N-(cyanomethyl)-4-methyl-L-prolinamide (66 mg, 0.123 mmol) in dry TBF (0.25 mL) under dry nitrogen was gradually added a total of 3 equivalents of MeSO3H (30 mL, 0.39 mmol) over a period of 1 hour in portions of 1–2 equivalents at a time and the reaction mixture was stirred overnight. Aqueous sat. NaHCO3 was added carefully and the product was extracted with EtOAc (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (HOH/MeOH/CH2Cl2, 1/9/90) to afford (4S)-1-(4-chloro-4′-piperazin-1-yl-1,1′-biphenyl-3-yl)-N-(cyanomethyl)-4-methyl-L-prolinamide. MS (-APCI): 436.2 [M−1]−.

Workup

  1. extractionthe product was extracted with EtOAc (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (HOH/MeOH/CH2Cl2, 1/9/90)

Sources & evidence

ORD record
ord-89774af0030641c599e64c517dd56667
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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