N,beta,beta-trimethyl-L-phenylalanyl-N1-[(1S,2E)-3-(ethoxysulfonyl)-1-isopropylprop-2-enyl]-N1,3-dimethyl-L-valinamide → N,beta,beta-trimethyl-L-phenylalanyl-N1-[(1S,2E)-1-isopropyl-3-sulfoprop-2-enyl]-N1,3-dimethyl-L-valinamide

HRID 133817Notes

Reaction equation

HRID 133817 reaction equation
[CH3:1][NH:2][C@H:3]([C:13]([NH:15][C@H:16]([C:21]([N:23]([C@@H:25]([CH:34]([CH3:36])[CH3:35])/[CH:26]=[CH:27]/[S:28]([O:31]CC)(=[O:30])=[O:29])[CH3:24])=[O:22])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:14])[C:4]([CH3:12])([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][NH:2][C@H:3]([C:13]([NH:15][C@H:16]([C:21]([N:23]([C@@H:25]([CH:34]([CH3:36])[CH3:35])/[CH:26]=[CH:27]/[S:28]([OH:31])(=[O:30])=[O:29])[CH3:24])=[O:22])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:14])[C:4]([CH3:11])([CH3:12])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 11706341N,beta,beta-trimethyl-L-phenylalanyl-N1-[(1S,2E)-3-(ethoxysulfonyl)-1-isopropylprop-2-enyl]-N1,3-dimethyl-L-valinamide

Product 1

HCID 86596602N,beta,beta-trimethyl-L-phenylalanyl-N1-[(1S,2E)-1-isopropyl-3-sulfoprop-2-enyl]-N1,3-dimethyl-L-valinamideYield 35.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

A solution of N,β,β-trimethyl-L-phenylalanyl-N1-[(1S,2E)-3-(ethoxysulfonyl)-1-isopropylprop-2-enyl]-N1,3-dimethyl-L-valinamide (30 mg, 0.057 mmol) from Example 63 in acetone (1 mL) is treated with tetrabutylammonium iodide (21 mg, 0.057 mmol). The reaction mixture is refluxed for 9 h, and then stirred at room temperature overnight. The solvent is removed. The residue is purified by reversal phase HPLC (mobile phase A: 0.1% TFA/5% acetonitrile/H2O, mobile phase B: 100% acetonitrile) to give 10 mg (28%) of the title compound as a white solid. HRMS (ESI) calcd for C25H41N3O5S [M+H] 496.2840, found 498.2840.

Workup

  1. temperatureThe reaction mixture is refluxed for 9 h
  2. customThe solvent is removed
  3. customThe residue is purified by reversal phase HPLC (mobile phase A: 0.1% TFA/5% acetonitrile/H2O, mobile phase B: 100% acetonitrile)

Sources & evidence

ORD record
ord-2d9696d48edc49efa02c06178c205c32
Source dataset
uspto-grants-2008_06
Patent number
US07390910B2

Reaction notes

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