HCID 11504791, compound → HCID 86596603, compound

HRID 133818Notes

Reaction equation

HRID 133818 reaction equation
[CH3:1][NH:2][C@H:3]([C:13]([NH:15][C@H:16]([C:21]([N:23]([C@@H:25]([CH:35]([CH3:37])[CH3:36])/[CH:26]=[C:27](/[S:29]([O:32]CC)(=[O:31])=[O:30])\[CH3:28])[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:35]([CH3:37])[CH3:36])/[CH:26]=[C:27](/[S:29]([OH:32])(=[O:31])=[O:30])\[CH3:28])[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.[CH3:1][NH:2][C@H:3]([C:13]([NH:15][C@H:16]([C:21]([N:23]([C@@H:25]([CH:35]([CH3:37])[CH3:36])/[CH:26]=[C:27](\[S:29]([OH:32])(=[O:31])=[O:30])/[CH3:28])[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

5

Reactant 1

HCID 11504791HCID 11504791, compound

Product 2

HCID 86596603HCID 86596603, compoundYield 28%HCID 86596604HCID 86596604, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

A solution of N,β,β-trimethyl-L-phenylalanyl-N1-[(1S,2E)-3-(ethoxysulfonyl)-1-isopropylbut-2-enyl]-N1,3-dimethyl-L-valinamide (30 mg, 0.046 mmol, from Example 65) in acetone (2 mL) is treated with tetrabutylammonium iodide (20 mg, 0.055 mmol). The reaction mixture is refluxed for 7 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 12 mg (28%) of N,β,β-trimethyl-L-phenylalanyl-N1-[(1S,2E)-1-isopropyl-3-sulfobut-2-enyl] N1,3-dimethyl-L-valinamide as a white solid and 2 mg of N,β,β-trimethyl-L-phenylalanyl-N1-[(1S,2Z)-1-isopropyl-3-sulfobut-2-enyl]-N1,3-dimethyl-L-valinamide

Workup

  1. temperatureThe reaction mixture is refluxed for 7 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-21e3216e0b7b40e78b0d39403b21cfb5
Source dataset
uspto-grants-2008_06
Patent number
US07390910B2

Reaction notes

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