HCID 131727504, compound → Phe(3-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

HRID 1988237Notes

Reaction equation

HRID 1988237 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[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[CH:5]=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]([CH3:17])[CH3:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[CH:5]=1

Participants

4

Reactant 1

HCID 131727504HCID 131727504, compound

Product 1

HCID 57729173Phe(3-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2Yield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of Boc-Phe(3-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(3-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (241 mg, 87%).

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-3fad5c34877344fbbac466207f1c0ce2
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

Loading…