Water → Z-Phe(4-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

HRID 1988232Notes

Reaction equation

HRID 1988232 reaction equation
[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([OH:13])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.[NH:24]([CH3:49])[C@H:25]([C:29]([N:31]([CH3:48])[C@H:32]([C:45]([NH2:47])=[O:46])[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:35]=1)=[O:30])[CH:26]([CH3:28])[CH3:27].O>C1COCC1>[NH:1]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@H:2]([C:11]([N:24]([CH3:49])[C@H:25]([C:29]([N:31]([CH3:48])[C@H:32]([C:45]([NH2:47])=[O:46])[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([C:41]([CH3:44])([CH3:42])[CH3:43])[CH:35]=1)=[O:30])[CH:26]([CH3:28])[CH3:27])=[O:13])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([F:10])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7020267(S)-2-(((Benzyloxy)carbonyl)amino)-3-(4-fluorophenyl)propanoic acidHCID 131722752N-Me-Val-N-Me-Tyr(3-tBu)-NH2

Product 1

HCID 131727502Z-Phe(4-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2Yield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Z-Phe(4-F)—OH (1.09 g, 3.44 mmol), N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (1.04 g, 2.87 mmol) and CMPI (878 mg, 3.44 mmol) in THF (30 ml), TEA (0.96 ml, 6.88 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: n-hexane:ethyl acetate=1:3) to give Z-Phe(4-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (1.73 g, 91%).

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-c4f25e93c12f4065a50008f78c7ac915
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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