Phenol → HCID 131727344, compound

HRID 1781974Notes

Reaction equation

HRID 1781974 reaction equation
C(O)(C(F)(F)F)=[O:2].N[C@@H](C(N[C@@H](C(N[C@@H](C(N[C@@H](C(N[C@@H](C(N[C@@H](C(N[C@@H](C(N[C@@H]([C:76]([NH:78][CH2:79][C:80]([NH:82][C@@H:83]([C:92]([NH2:94])=[O:93])[CH2:84][C:85]1[CH:90]=[CH:89][C:88]([OH:91])=[CH:87][CH:86]=1)=[O:81])=[O:77])CCCC)=O)CCCC)=O)CCCC)=O)CCCNC(=N)N)=O)CCCC)=O)CCCC)=O)CCCC)=O)CCCNC(=N)N.C(O)(C(F)(F)F)=O.C1(O)C=CC=CC=1.[C:109]1([CH3:115])[CH:114]=CC=C[CH:110]=1>C1COCC1>[NH:78]([C:76]([O:77][C:109]([CH3:115])([CH3:114])[CH3:110])=[O:2])[CH2:79][C:80]([NH:82][C@@H:83]([C:92]([NH2:94])=[O:93])[CH2:84][C:85]1[CH:86]=[CH:87][C:88]([OH:91])=[CH:89][CH:90]=1)=[O:81]

Participants

6

Reactant 4

HCID 996PhenolHCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 178446020HCID 178446020, compound

Product 1

HCID 131727344HCID 131727344, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The deprotected peptide SF1257-13 (TFA-(D)Arg-(D)Nle-(D)Nle-(D)Nle-(D)Arg-(D)Nle-(D)Nle-(D)Nle-Gly-(D)Tyr-NH2 (SEQ ID NO:1) is made by slowly adding TFA (A×3 l) to a mixture of SF1257-12 (A kg) and phenol (A×0.1 kg) in toluene and THF while maintaining the temperature at ≦18° C. The reaction mixture is allowed to warm up to room temperature. Following completion of cleavage, the solvent is diluted with THF and then concentrated in vacuo. Residual TFA is removed by azeotropic distillation with toluene. The residue is poured into a mixture of petroleum ether and diisopropyl ether. The solid is filtered, washed with diisopropyl ether and dried in vacuo.

Workup

  1. concentrationconcentrated in vacuo
  2. customResidual TFA is removed by azeotropic distillation with toluene
  3. additionThe residue is poured into a mixture of petroleum ether and diisopropyl ether
  4. filtrationThe solid is filtered
  5. washwashed with diisopropyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ca9f5351d49a4a978457ad82bd1fbd60
Source dataset
uspto-grants-2009_03
Patent number
US07498309B2

Reaction notes

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