Nitrogen → HCID 178512906, 화합물

HRID 1108548

반응식

HRID 1108548 반응식
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:30]([NH:32][CH2:33][C:34]([NH:36][C@H:37]([C:55]([OH:57])=[O:56])[CH2:38][CH2:39][CH2:40][NH:41][C:42](=[NH:54])[NH:43]S(C1C=CC(C)=CC=1)(=O)=O)=[O:35])=[O:31])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:29])[N:8](C(OCC1C=CC=CC=1)=O)C(OCC1C=CC=CC=1)=O.[S:65]1[CH:69]=[CH:68][N:67]=[CH:66]1.C1(OC)C=CC=CC=1.N#N>CSCC.CCOCC.CCCCCC>[NH2:1][C@@H:2]([C:30]([NH:32][CH2:33][C:34]([NH:36][C@H:37]([C:55]([OH:57])=[O:56])[CH2:38][CH2:39][CH2:40][NH:41][C:42](=[NH:43])[NH2:54])=[O:35])=[O:31])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:29].[S:65]1[CH:69]=[CH:68][N:67]=[CH:66]1

참가 물질

6

반응물 3

HCID 947NitrogenHCID 7519AnisoleHCID 178427556HCID 178427556, 화합물

생성물 1

HCID 178512906HCID 178512906, 화합물수율 60%

시약·촉매·용매 2

HCID 12230Ethyl methyl sulfide촉매HCID 21584099Diethylether hexane용매

반응 조건

온도
0 °C

실험 절차

A 100 mg portion of Boc-(D)-Arg(Cbz2)-Gly-Arg(Tos)-Thiazole, 1 mL of anisole and 4 drops of MeSEt were placed in HF-cleavage vessel and cooled under liquid N2. HF (10 mL) was then condensed into the reaction mixture and stirred at 0° C. for 1.25 h. HF was removed under vacuum to give a gum-like residue which was titrated with 20 mL of 50% Et2O-hexane and the organic wash removed by filtration. The gum residue was dissolved in 30 mL of 30% aq. HOAc and filtered through the above sintered funnel. The filtrate was lyophilized to give a powder which was purified by RP-HPLC to give 28 mg (60% yield) of (D)-Arg-Gly-Arg-thiazole. FAB-MS (M+H)+ =455.2

후처리

  1. customcondensed into the reaction mixture
  2. customHF was removed under vacuum
  3. customto give a gum-like residue which
  4. washthe organic wash
  5. customremoved by filtration
  6. dissolutionThe gum residue was dissolved in 30 mL of 30% aq. HOAc
  7. filtrationfiltered through the above sintered funnel
  8. customto give a powder which
  9. customwas purified by RP-HPLC

출처 및 근거

ORD 기록
ord-283db2cfbe884f068a53863e057d09e1
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06069130

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