Boc-Phe(2-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 → Phe(2-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

HRID 1988239Notes

Reaction equation

HRID 1988239 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:11]([N:13]([CH3:38])[C@H:14]([C:18]([N:20]([CH3:37])[C@H:21]([C:34]([NH2:36])=[O:35])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=1)=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH2:3][C:4]1[C:5]([F:10])=[CH:6][CH:7]=[CH:8][CH:9]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:1][C@H:2]([C:11]([N:13]([CH3:38])[C@H:14]([C:18]([N:20]([CH3:37])[C@H:21]([C:34]([NH2:36])=[O:35])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:31])([CH3:32])[CH3:33])[CH:24]=1)=[O:19])[CH:15]([CH3:16])[CH3:17])=[O:12])[CH2:3][C:4]1[C:5]([F:10])=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 131727505Boc-Phe(2-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

Product 1

HCID 57729115Phe(2-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2Yield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of Boc-Phe(2-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (0.33 g, 0.525 mmol) in methylene chloride (3 ml), TFA (1.5 ml) was added, stirred for 15 min. and then evaporated to remove the solvent under reduced pressure. The residue was mixed with methylene chloride, washed with a saturated aqueous NaHCO3 solution, 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: chloroform:methanol:aqueous ammonia=40:1:0.1) to give Phe(2-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (235 mg, 85%).

Workup

  1. customevaporated
  2. customto remove the solvent under reduced pressure
  3. additionThe residue was mixed with methylene chloride
  4. washwashed with a saturated aqueous NaHCO3 solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-01509db9dce14bbea592d6646822b480
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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