Methanesulfonic Acid → HCID 10111943, compound

HRID 1744050Notes

Reaction equation

HRID 1744050 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C@@H:7]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]3)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6])#[N:2].CS(O)(=O)=O.C([O-])(O)=O.[Na+]>>[C:1]([CH2:3][NH:4][C:5](=[O:6])[C@@H:7]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]3)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])#[N:2]

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 86594552HCID 86594552, compound

Product 1

HCID 10111943HCID 10111943, compound

Procedure

To tert-butyl 4-{4′-[((1S)-1-{[(cyanomethyl)amino]carbonyl}-3-methylbutyl)amino][1,1′-biphenyl]-4-yl}-1-piperazinecarboxylate (122 mg, 0.242 mmol) in dry TB (5 mL) under dry nitrogen was gradually added a total of 10 equivalents of MeSO3H (160 μL, 2.42 mmol) over a period of 5 days in portions of 1–2 equivalents at a time. Aqueous sat. NaHCO3 was added carefully and the product was extracted with EtOAc (3×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (NH4OH/MeOH/CH2Cl2, 1.5/13.5/85) to afford (2S)-N-(cyanomethyl)-4-methyl-2-{[4′-(1-piperazinyl)[1,1′-biphenyl]-4-yl]amino}pentanamide. MS (+ESI): 406.9 [M+1]+.

Workup

  1. extractionthe product was extracted with EtOAc (3×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (NH4OH/MeOH/CH2Cl2, 1.5/13.5/85)

Sources & evidence

ORD record
ord-a0c349cde56a4e1fb171aad495f4f71c
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

Loading…