HCID 151180、化合物 → HCID 131722374、化合物

HRID 634626ノート

反応式

HRID 634626 の反応式
[NH:1]([C:18]([O:20]CC1C=CC=CC=1)=O)[C@H:2]([C:10]([NH:12][C@@H:13]([C:15]([OH:17])=[O:16])[CH3:14])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].[NH:30]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[C@@H:31](C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O)[CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37].N[C@H](C(N[C@@H](C(O)=O)C)=O)CC1C=CC=CC=1>CO.C(O)=O.[Pd].O1CCOCC1.O>[NH:30]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[C@@H:31]([C:18]([NH:1][C@H:2]([C:10]([NH:12][C@@H:13]([C:15]([OH:17])=[O:16])[CH3:14])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:20])[CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37]

参加物

10

反応物 4

HCID 151180HCID 151180、化合物HCID 3008147D-Alanine, N-[(phenylmethoxy)carbonyl]-L-phenylalanyl-HCID 14392679HCID 14392679、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 131722374HCID 131722374、化合物

試薬・触媒・溶媒 5

HCID 23938Palladium触媒HCID 284Formic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

6.5 g (18.0 mmol) of Z-Phe-D-Ala-OH was dissolved in 15 ml methanol and 2 ml formic acid. 0.2 g palladium catalyst was added and hydrogen was passed through the solution for 3 hours. The catalyst was removed by filtration, and the solvents were evaporated under vacuum. The residue was flooded with ether. The precipitate was filtered off, rinsed with ether and dried. The yield of H-Phe-D-Ala-OH was 5.3 g (98.1%). Rf=0.01 in chloroform:ethyl acetate:methanol:acetic acid=6:3:1:0.1. Rf=0.45 in acetic acid:chloroform:methanol=1:3:2:2. 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.

後処理

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

出典と根拠

ORDレコード
ord-6a235c9db3c04720991ff23d47d8940e
出典データセット
uspto-grants-2001_02
特許番号
US06184208B2

反応ノート

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