Water → 2-Tert-butoxycarbonylamino-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamide

HRID 1988281Notes

Reaction equation

HRID 1988281 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].[C:16]([C:20]1[CH:21]=[C:22]([CH2:27][CH:28]([NH2:34])[C:29]2[S:30][CH:31]=[CH:32][N:33]=2)[CH:23]=[CH:24][C:25]=1[OH:26])([CH3:19])([CH3:18])[CH3:17].O>C1COCC1>[C:16]([C:20]1[CH:21]=[C:22]([CH2:27][CH:28]([NH:34][C:6](=[O:8])[CH:2]([NH:1][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:3]([CH3:4])[CH3:5])[C:29]2[S:30][CH:31]=[CH:32][N:33]=2)[CH:23]=[CH:24][C:25]=1[OH:26])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 83693Boc-L-ValineHCID 178192062-(3-Tert-butyl-4-hydroxylphenyl)-1-(thiazol-2-yl)ethylamine

Product 1

HCID 876058412-Tert-butoxycarbonylamino-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamideYield 106%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Boc-Val-OH (890 mg, 4.09 mmol), 2-(3-tert-butyl-4-hydroxyphenyl)-1-(thiazol-2-yl)ethylamine (1.03 g, 3.73 mmol) and CMPI (653 mg, 1.05 mmol) in THF (10 ml), TEA (1 ml) 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 sodium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1), giving the titled compound (1.88 g, 99%).

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 sodium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-21f82f36e5a84cf49f8a2bfadfbb73ff
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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