Water → 2-Benzyloxycarbonylamino-3-methylbutyric acid 2-(3-t-butyl-4-hydroxyphenyl)-1-(1,3,4-oxadiazol-2-yl)ethylamide

HRID 1988268Notes

Reaction equation

HRID 1988268 reaction equation
[C:1]([N:11](C)[C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:20]([C:24]1[CH:25]=[C:26]([CH2:31][CH:32]([NH2:38])[C:33]2[O:34][CH:35]=[N:36][N:37]=2)[CH:27]=[CH:28][C:29]=1[OH:30])([CH3:23])([CH3:22])[CH3:21].O>C1COCC1>[C:20]([C:24]1[CH:25]=[C:26]([CH2:31][CH:32]([NH:38][C:16](=[O:18])[CH:12]([NH:11][C:1]([O:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2])[CH:13]([CH3:14])[CH3:15])[C:33]2[O:34][CH:35]=[N:36][N:37]=2)[CH:27]=[CH:28][C:29]=1[OH:30])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 178192112-(3-t-Butyl-4-hydroxyphenyl)-1-(1,3,4-oxadiazol-2-yl)ethylamine

Product 1

HCID 876059742-Benzyloxycarbonylamino-3-methylbutyric acid 2-(3-t-butyl-4-hydroxyphenyl)-1-(1,3,4-oxadiazol-2-yl)ethylamideYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Z-N-Me-Val-OH (914 mg, 3.45 mmol), 2-(3-t-butyl-4-hydroxyphenyl)-1-(1,3,4-oxadiazol-2-yl)ethylamine (0.75 g, 2.87 mmol) and CMPI (881 mg, 3.45 mmol) in THF (30 ml), TEA (0.96 ml) was added under cooling with ice and stirred at room temperature for 2 hours. 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: ethyl acetate:n-hexane=1:1), giving 2-benzyloxycarbonylamino-3-methylbutyric acid 2-(3-t-butyl-4-hydroxyphenyl)-1-(1,3,4-oxadiazol-2-yl)ethylamide (1.28 g, 88%).

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-4c6f800783fb4e49b4898f69c37a0642
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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