Hydrochloric Acid → HCID 178447157、化合物

HRID 1905319ノート

反応式

HRID 1905319 の反応式
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

参加物

9

反応物 6

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

生成物 1

HCID 178447157HCID 178447157、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒3 回HCID 8471Triethylamine溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-412eb764db1549d3b0107f8f1c7c0e0c
出典データセット
uspto-grants-1989_06
特許番号
US04841067

反応ノート

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