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

HRID 1988248Notes

Reaction equation

HRID 1988248 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:23][C:24](=[O:31])[CH:25]([NH:29][CH3:30])[CH:26]([CH3:28])[CH3:27])[C:14](=[O:22])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[NH:32]([C:45]([O:47][C:48]([CH3:51])(C)C)=[O:46])[C@H:33]([C:42]([OH:44])=O)[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1.O.[CH2:53]1COC[CH2:54]1>>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH:23][C:24](=[O:31])[CH:25]([N:29]([C:42](=[O:44])[CH:33]([NH:32][C:45]([O:47][CH2:48][CH2:51][CH2:53][CH3:54])=[O:46])[CH2:34][C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)[CH3:30])[CH:26]([CH3:27])[CH3:28])[C:14](=[O:22])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanineHCID 867608933-Methyl-2-methylaminobutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamide

Product 1

HCID 867608962-((2-butoxycarbonylamino-3-(4-fluorophenyl)propionyl)-N-methylamino)-3-methylbutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamideYield 85%

Procedure

To a solution of 3-methyl-2-methylaminobutyric acid 2-(3-tert-butyl-4-hydroxyphenyl)-1-(2-pyridylcarbamoyl)ethylamide (1.25 g, 2.93 mmol), Boc-Phe(4-F)-OH (1.08 g, 3.81 mmol) and CMPI (973 mg, 3.81 mmol) in THF 19 ml, TEA (0.94 ml, 6.74 mmol) was added under cooling with ice and stirred for 4 hours under cooling with ice. 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 the titled compound (1.72 g, 85%).

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-16f5d052f93549be985e73e77c7e102c
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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