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

HRID 1988276Notes

Reaction equation

HRID 1988276 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH2:19])[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].[N:20]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([CH3:28])[C@H:21]([C:25](O)=[O:26])[CH:22]([CH3:24])[CH3:23].O>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:19][C:25](=[O:26])[CH:21]([N:20]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH3:28])[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])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 7010608Boc-N-methyl-L-valineHCID 178192062-(3-Tert-butyl-4-hydroxylphenyl)-1-(thiazol-2-yl)ethylamine

Product 1

HCID 867609042-(N-tert-butoxycarbonyl-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-tert-butyl-4-hydroxylphenyl)-1-(thiazol-2-yl)ethylamine (4.67 g, 16.64 mmol), Boc-N-Me-Val-OH (5.0 g, 21.63 mmol) and CMPI (5.53 g, 21.63 mmol) in THF (110 ml), TEA (5.33 ml, 38.27 mmol) was added under cooling with ice and stirred at room temperature overnight. The reaction mixture was mixed with water and extracted with ethyl acetate. The organic layer was washed with 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: methanol:aqueous ammonia:methylene chloride=3:0.1:100), giving the titled compound (8.10 g, 100%).

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-0ffe183d62f948e1b2827bff7f41e312
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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