Hydrochloric Acid → HCID 178447157, 화합물

HRID 1905319노트

반응식

HRID 1905319 반응식
C1(CC(CC(=O)NCCC2C=CC=CC=2)C(N(C(=O)[C@H](CC2N=CNC=2)N)N)=O)C2C(=CC=CC=2)C=CC=1.Cl.N(OCCC(C)C)=O.[C:48]1([CH2:58][CH:59]([CH2:75][C:76](=[O:86])[NH:77][CH2:78][CH2:79][C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)[C:60]([NH:62][C@H:63]([C:70]([N:72]=[N+]=[N-])=[O:71])[CH2:64][C:65]2[N:69]=[CH:68][NH:67][CH:66]=2)=[O:61])[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=[CH:50][CH:49]=1.[N-]=[N+]=[N-].N[C@@H:91]([CH2:102][CH:103]([CH3:105])[CH3:104])[CH:92]([OH:101])[C:93]([O:95][CH2:96][CH2:97][CH:98]([CH3:100])[CH3:99])=[O:94]>CN(C)C=O.C(N(CC)CC)C>[C:48]1([CH2:58][CH:59]([CH2:75][C:76](=[O:86])[NH:77][CH2:78][CH2:79][C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)[C:60]([NH:62][C@H:63]([C:70]([NH:72][C@@H:91]([CH2:102][CH:103]([CH3:105])[CH3:104])[CH:92]([OH:101])[C:93]([O:95][CH2:96][CH2:97][CH:98]([CH3:99])[CH3:100])=[O:94])=[O:71])[CH2:64][C:65]2[N:69]=[CH:68][NH:67][CH:66]=2)=[O:61])[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=[CH:50][CH:49]=1

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 33558AzideHCID 56608254isoamyl (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoateHCID 178511798HCID 178511798, 화합물HCID 178514640HCID 178514640, 화합물

생성물 1

HCID 178447157HCID 178447157, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매3회HCID 8471Triethylamine용매2회

실험 절차

To a suspension of 200 mg of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidine hydrazide in 5 ml of N,N-dimethylformamide were added successively dropwise 0.25 ml of a dry 5.1N-hydrogen chloride in N,N-dimethyformamide solution and 0.07 ml of isoamyl nitrite with stirring at -20° C. After disappearance of hydrazide compound, the reaction mixture was cooled to -30° C., and neutralized by adding 0.2 ml of triethylamine to prepare a solution of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)-propionyl]-L-histidine azide. The azide solution prepared was added dropwise to 110 mg of isoamyl (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoate and 0.1 ml of triethylamine in 2 ml of dry N,N-dimethylformamide under ice-cooling, and the mixture was stirred for 16 hours. The reaction mixture was evaporated under reduced pressure, and a 5% aqueous sodium bicarbonate solution was added to the residue. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The pressure was purified by silica gel column chromatography (eluent: chloroform/ethanol=10/1 by volume) to obtain 52 mg of isoamyl (2RS,3S)-3-{N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidyl}amino-2-hydroxy-5-methylhexanoate as a white powder.

후처리

  1. temperaturecooling
  2. customThe reaction mixture was evaporated under reduced pressure
  3. additiona 5% aqueous sodium bicarbonate solution was added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe pressure was purified by silica gel column chromatography (eluent: chloroform/ethanol=10/1 by volume)

출처 및 근거

ORD 기록
ord-412eb764db1549d3b0107f8f1c7c0e0c
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04841067

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