D-Alanine → D-Alanine, N-[(phenylmethoxy)carbonyl]-L-phenylalanyl-

HRID 1067208Notes

Reaction equation

HRID 1067208 reaction equation
[NH:1]([C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C@H:2]([C:10]([O:12]C1C(F)=C(F)C(F)=C(F)C=1F)=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:34][C@@H:35]([C:37]([OH:39])=[O:38])[CH3:36]>C1COCC1.O>[NH:1]([C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])[C@H:2]([C:10]([NH:34][C@@H:35]([C:37]([OH:39])=[O:38])[CH3:36])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 71080D-AlanineHCID 13993489HCID 13993489, compound

Product 1

HCID 3008147D-Alanine, N-[(phenylmethoxy)carbonyl]-L-phenylalanyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

9.68 g (20.0 mmol) of Z-Phe-OPfp was dissolved in 20 ml of THF and to this was added 2.3 g (25.6 mmol) of H-D-Ala-OH dissolved in 5 ml water, pH 8.5. The reaction mixture was stirred for one day and one night at room temperature. The solvents were removed by evaporation under vacuum, 70 ml ethyl acetate was added, and the mixture was acidified to pH 2-3 by the addition of 70 ml of 2% sulfuric acid. The peptide was extracted twice with 70 ml ethyl acetate, washed with saturated sodium chloride solution to neutral pH, then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under vacuum, leaving a thick oil. The product was crystallized from ether/hexane. The yield was 7.6 g (97.7%), melting point was 153-154° C. Rf=0.40 in chloroform:ethyl acetate:methanol:acetic acid=6:3:1:0.1. Rf=0.53 in acetic acid:chloroform:methanol=0.5:16:1. Rf=0.58 in acetic acid:chloroform:methanol=0.5:9:1. [α]20D=+3.2 (C=1, CH3OH).

Workup

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

Sources & evidence

ORD record
ord-634918bb0a44437c815cdea89f100479
Source dataset
uspto-grants-2001_06
Patent number
US06248716B1

Reaction notes

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