Methanesulfonic Acid → HCID 21071621, compound

HRID 1371933Notes

Reaction equation

HRID 1371933 reaction equation
CS(O)(=O)=O.C(OC([N:13]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][CH2:32][CH3:33])[CH:25]=1)[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)=O)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>ClCCl.C(O)(=O)C.CO>[Cl:22][C:18]1[CH:17]=[C:16]([CH2:15][CH2:14][NH:13][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][CH2:32][CH3:33])[CH:25]=2)[CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 21071685HCID 21071685, compound

Product 1

HCID 21071621HCID 21071621, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Add methanesulfonic acid (70 uL) to a solution of N-t-Butoxycarbonyl-N-2-(3-chlorophenyl)ethyl-3-propoxybenzylamine in dichloromethane (4 mL) and agitate the mixture for 3 hours at room temperature. Add 10% aqueous Na2CO3 (2 mL), separate the layers, and concentrate the organic layer in a nitrogen stream to give a residue. Dissolve the residue in 4 mL of 5% acetic acid in methanol and pass through a 1 gm SCX column, eluting with 1 M ammonia in methanol to give the title compound: MS (ES+): m/e (M+1). HPLC (10–90% water/acetonitrile over 7.5 min, Tr=4.490 min).

Workup

  1. customseparate the layers
  2. concentrationconcentrate the organic layer in a nitrogen stream
  3. customto give a residue
  4. washpass through a 1 gm SCX column, eluting with 1 M ammonia in methanol

Sources & evidence

ORD record
ord-6d4c2f44141043be81af51fa180722de
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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