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

HRID 1988272Notes

Reaction equation

HRID 1988272 reaction equation
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[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:21]([CH3:45])[C@H:22]([C:26]([NH:28][C@H:29]([C:42]([NH2:44])=[O:43])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH:32]=1)=[O:27])[CH:23]([CH3:25])[CH3:24].O>C1COCC1>[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:2]([C:11]([N:21]([CH3:45])[C@H:22]([C:26]([NH:28][C@H:29]([C:42]([NH2:44])=[O:43])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([C:38]([CH3:39])([CH3:41])[CH3:40])[CH:32]=1)=[O:27])[CH:23]([CH3:25])[CH3:24])=[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 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanineHCID 131722732N-Me-Val-Tyr(3-tBu)-NH2

Product 1

HCID 131727517Boc-Phe(4-F)-N-Me-Val-Tyr(3-tBu)-NH2Yield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Boc-Phe(4-F)-OH (890 mg, 3.14 mmol), N-Me-Val-Tyr(3-tBu)-NH2 (1 g, 2.86 mmol) and CMPI (804 mg, 3.15 mmol) in THF (20 ml), TEA (1.2 ml, 7.16 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: acetone:n-hexane=1:2), giving Boc-Phe(4-F)-N-Me-Val-Tyr(3-tBu)-NH2 (1.5 g, 85%).

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-cfec7b9633704949818a79d50552537e
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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