Hydrochloric Acid → HCID 178496810、化合物

HRID 1905322ノート

反応式

HRID 1905322 の反応式
C1(CC(CC(=O)NCCC2C=CC=CC=2)C([N:15](C(=O)[C@H](CC2N=CNC=2)N)N)=O)C2C(=CC=CC=2)C=CC=1.Cl.[C:40]1([CH2:50][CH:51]([CH2:67][C:68](=[O:78])[NH:69][CH2:70][CH2:71][C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)[C:52]([NH:54][C@H:55]([C:62](N=[N+]=[N-])=[O:63])[CH2:56][C:57]2[N:61]=[CH:60][NH:59][CH:58]=2)=[O:53])[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1.[N-]=[N+]=[N-].Cl.[CH3:83][O:84][CH2:85][CH:86]([OH:93])[C@@H:87](N)[CH2:88][CH:89]([CH3:91])[CH3:90]>CN(C)C=O.N(OCCC(C)C)=O.C(N(CC)CC)C>[CH3:83][O:84][CH:85]([NH2:15])[CH:86]([OH:93])[C@@H:87]([C:62](=[O:63])[C@H:55]([CH2:56][C:57]1[N:61]=[CH:60][NH:59][CH:58]=1)[NH:54][C:52](=[O:53])[CH:51]([CH2:50][C:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1)[CH2:67][C:68](=[O:78])[NH:69][CH2:70][CH2:71][C:72]1[CH:73]=[CH:74][CH:75]=[CH:76][CH:77]=1)[CH2:88][CH:89]([CH3:91])[CH3:90]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 33558AzideHCID 86743183(2RS, 3S)-3-amino-2-hydroxy-5-methylhexyl methyl ether hydrochlorideHCID 178511798HCID 178511798、化合物HCID 178514640HCID 178514640、化合物

生成物 1

HCID 178496810HCID 178496810、化合物

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒3 回HCID 8053Isoamyl Nitrite溶媒HCID 8471Triethylamine溶媒2 回

実験手順

To a suspension of 130 mg of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidine hydrazide in 6 ml of dry N,N-dimethylformamide were added successively dropwise 0.19 ml of a dry 5.1N-hydrogen chloride in N,N-dimethylformamide solution and 0.05 ml of isoamyl nitrite, and the mixture was stirred. After disappearance of hydrazide compound, the reaction mixture was cooled to -30° C., and neutralized by adding 0.14 ml of triethylamine to prepare a solution of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidine azide. The azide solution prepared was added drowise to a solution of 52 mg of (2RS, 3S)-3-amino-2-hydroxy-5-methylhexyl methyl ether hydrochloride and 0.05 ml of triethylamine in 2 ml of dry N,N-dimethylformamide under ice-cooling, and the mixture was stirred for 16 hours under ice-cooling. 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 washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by preparative silica gel thin layer chromatography (developing solvent: lower layer of chloroform/methanol/water32 8/3/1 by volume) to obtain 55 mg of (2RS, 3S)-3-{N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidyl}-amino-2-hydroxy-5-methylhexyl methyl ether as a white powder.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. customThe reaction mixture was evaporated under reduced pressure
  4. additiona 5% aqueous sodium bicarbonate solution was added to the residue
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by preparative silica gel thin layer chromatography (developing solvent: lower layer of chloroform/methanol/water32 8/3/1 by volume)

出典と根拠

ORDレコード
ord-5f5699e2d4d2410ab1ce600b31969d1f
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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