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

HRID 1988285Notes

Reaction equation

HRID 1988285 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:12]([N:14]([CH3:39])[C@H:15]([C:19]([N:21]([CH3:38])[C@H:22]([C:35]([NH2:37])=[O:36])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:25]=1)=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:3][C:4]1[C:5]([F:11])=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:1][C@H:2]([C:12]([N:14]([CH3:39])[C@H:15]([C:19]([N:21]([CH3:38])[C@H:22]([C:35]([NH2:37])=[O:36])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([C:31]([CH3:32])([CH3:34])[CH3:33])[CH:25]=1)=[O:20])[CH:16]([CH3:18])[CH3:17])=[O:13])[CH2:3][C:4]1[C:5]([F:11])=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 131727518Boc-Tyr(2-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

Product 1

HCID 57729155Tyr(2-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2Yield 97.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of Boc-Tyr(2-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (0.21 g, 0.326 mmol) in methylene chloride (3 ml), TFA (1.5 ml) was added and stirred for 15 min. The reaction mixture was concentrated under reduced pressure, mixed with a saturated aqueous NaHCO3 solution, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The resultant was evaporated to remove the solvent under reduced pressure, giving the titled compound (173 mg, 82%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionmixed with a saturated aqueous NaHCO3 solution
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customThe resultant was evaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-b22d79ecd6764c63bd30e682d6e14e9f
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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