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

HRID 634625노트

반응식

HRID 634625 반응식
[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

참가 물질

5

반응물 2

HCID 71080D-AlanineHCID 13993489HCID 13993489, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e55303210d7a4bcaa549b8ac3bed186c
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06184208B2

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