2-(N-tert-butoxycarbonyl-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide → 3-Methyl-2-methylaminobutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide

HRID 1988277Notes

Reaction equation

HRID 1988277 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:19][C:20](=[O:34])[CH:21]([N:25](C(OC(C)(C)C)=O)[CH3:26])[CH:22]([CH3:24])[CH3:23])[C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:19][C:20](=[O:34])[CH:21]([NH:25][CH3:26])[CH:22]([CH3:23])[CH3:24])[C:14]2[S:15][CH:16]=[CH:17][N:18]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 867609042-(N-tert-butoxycarbonyl-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide

Product 1

HCID 867609033-Methyl-2-methylaminobutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2-(N-tert-butoxycarbonyl-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide (8.03 g, 16.42 mmol) in methylene chloride (80 ml), TFA (40 ml) was added and stirred at room temperature for 30 min. The reaction mixture was evaporated to remove the solvent under reduced pressure; the thus obtained residue was mixed with methylene chloride, washed with a 2N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure. The thus obtained residue was subjected to silica gel column chromatography (developing solvent: acetone:hexane=1:2), giving two diastereoisomers A and B of the titled compound, A (2.37 g, 37%) being eluted first and then B (2.17 g, 34%). (A)

Workup

  1. customThe reaction mixture was evaporated
  2. customto remove the solvent under reduced pressure
  3. additionthe thus obtained residue was mixed with methylene chloride
  4. washwashed with a 2N aqueous sodium hydroxide solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-2dd4becd7e5a46e2b01ceeec288c4656
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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