Water → 2-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamide

HRID 1988246Notes

Reaction equation

HRID 1988246 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][C:22]=1[OH:23])[CH2:8][C@@H:9]([C:11]([N-:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:12])[NH2:10])([CH3:4])([CH3:3])[CH3:2].[C:24]([N:34]([CH3:42])[C@H:35]([C:39](O)=[O:40])[CH:36]([CH3:38])[CH3:37])([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25].O>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH2:8][CH:9]([NH:10][C:39](=[O:40])[CH:35]([N:34]([C:24]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25])[CH3:42])[CH:36]([CH3:38])[CH3:37])[C:11](=[O:12])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:20]=[CH:21][C:22]=1[OH:23])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 178440897HCID 178440897, compound

Product 1

HCID 867608942-(N-benzyloxycarbonyl-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamideYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-tert-butyl-4-hydroxyphenylalanyl (2-pyridyl)amide (1.48 g, 4.73 mmol), Z-N-Me-Val-OH (1.63 g, 6.15 mmol) and CMPI (1.57 g, 6.15 mmol) in THF 30 ml, TEA (1.5 ml, 10.88 mmol) was added under cooling with ice and stirred for 3 hours under cooling with ice. The 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=1:2), giving the titled compound (1.74 g, 65%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 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-0c513f773cba4e6dbb167847c5a4dd7c
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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