HCID 151180, compound → HCID 131722374, compound

HRID 1067209Notes

Reaction equation

HRID 1067209 reaction equation
[NH:1]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@@H:2]([C:17]([O:19]C1C(F)=C(F)C(F)=C(F)C=1F)=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[NH2:38][C@H:39]([C:47]([NH:49][C@@H:50]([C:52]([OH:54])=[O:53])[CH3:51])=[O:48])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O1CCOCC1.O>[NH:1]([C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[C@@H:2]([C:17]([NH:38][C@H:39]([C:47]([NH:49][C@@H:50]([C:52]([OH:54])=[O:53])[CH3:51])=[O:48])[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:19])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

Participants

5

Reactant 2

HCID 151180HCID 151180, compoundHCID 14392679HCID 14392679, compound

Product 1

HCID 131722374HCID 131722374, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

8.0 g (15.0 mmol) of pentafluorophenyl ester of Boc-D-Orn(Z)-OPfp was dissolved in 15 ml dioxane. To this was added with mixing 4.3 g (17.7 mmol) H-Phe-D-Ala-OH dissolved in water with pH 8.5. The reaction mixture was stirred for a day and a night at room temperature. The solvents were evaporated under vacuum, 70 ml ethyl acetate was added, and the mixture was acidified to pH 2-3 by the addition of 2% sulfuric acid solution. The peptide was extracted twice with 70 ml ethyl acetate, washed with saturated sodium chloride solution to neutral pH and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under vacuum leaving a thick oil. The product was crystallized from ethyl acetate with ether and hexane. The yield was 6.92 g (74.4%), and the melting point was 145° C. Rf=0.44 in acetic acid:chloroform;methanol=0.5:16:1. Rf=0.32 in chloroform:ethyl acetate:methanol=6:3:1.

Workup

  1. additionTo this was added
  2. customThe solvents were evaporated under vacuum, 70 ml ethyl acetate
  3. additionwas added
  4. additionthe mixture was acidified to pH 2-3 by the addition of 2% sulfuric acid solution
  5. extractionThe peptide was extracted twice with 70 ml ethyl acetate
  6. washwashed with saturated sodium chloride solution to neutral pH
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed by evaporation under vacuum
  9. customleaving a thick oil
  10. customThe product was crystallized from ethyl acetate with ether and hexane

Sources & evidence

ORD record
ord-61fe2ff0c6da493dab50276273095d97
Source dataset
uspto-grants-2001_06
Patent number
US06248716B1

Reaction notes

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