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

HRID 1988235Notes

Reaction equation

HRID 1988235 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][C:7]([Cl:10])=[CH:6][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]([CH3:16])[CH3:17])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 131727503Boc-Phe(4-Cl)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

Product 1

HCID 57729126Phe(4-Cl)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2Yield 93.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of Boc-Phe(4-Cl)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (0.45 g, 0.697 mmol) in methylene chloride (4 ml), TFA (3 ml) was added, stirred for 20 min. and evaporated to remove the solvent under reduced pressure. The thus obtained residue was mixed with a saturated aqueous NaHCO3 solution, and extracted with methylene chloride. The organic layer was dried over anhydrous sodium 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=30:1:0.1) to give Phe(4-Cl)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (355 mg, 93%). EI-MS:544 and 546 (M+)

Workup

  1. customevaporated
  2. customto remove the solvent under reduced pressure
  3. additionThe thus obtained residue was mixed with a saturated aqueous NaHCO3 solution
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customevaporated
  7. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-cfc04c07f96c458d9e4c9832ec5e1d48
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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