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Triethylamine → Amino-2-ethyl-4-hydroxy-7-methyloctanoic acid isobutylamide

HRID 374685
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인쇄 미리보기

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HRID 374685 반응식
[NH2:1][C@H](C(O)=O)CCCC.C(N(CC)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.Cl.[CH2:35]([NH:39][C:40](=[O:53])[CH:41]([CH2:51][CH3:52])[CH2:42][C@H:43]([OH:50])[C@@H:44](N)[CH2:45][CH:46]([CH3:48])[CH3:47])[CH:36]([CH3:38])[CH3:37]>CN(C=O)C.C(OCC)(=O)C>[CH2:35]([NH:39][C:40](=[O:53])[C:41]([NH2:1])([CH2:51][CH3:52])[CH2:42][CH:43]([OH:50])[CH2:44][CH2:45][CH:46]([CH3:48])[CH3:47])[CH:36]([CH3:38])[CH3:37]
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 21236CaprineHCID 199401P,P-Diphenylphosphinic azideHCID 14582181(2RS,4S,5S)-5-amino-2-ethyl-4-hydroxy-7-methyloctanoic acid isobutylamide monohydrochloride

생성물 1

HCID 54242229Amino-2-ethyl-4-hydroxy-7-methyloctanoic acid isobutylamide

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
-15 °C

실험 절차

20.7 mg of L-N-[(2R or S)-5-ethylthio-2-(naphthylmethyl)pentanoyl]norleucine was dissolved in 0.5 ml of dry DMF. Then, 27.4 μl of triethylamine, 12.9 μl of DPPA and 20 mg of (2RS,4S,5S)-5-amino-2-ethyl-4-hydroxy-7-methyloctanoic acid isobutylamide monohydrochloride was added thereto under stirring at -15° C. The mixture was stirred at the same temperature for one hour and then at 5° C. overnight. The reaction solution was diluted with 20 ml of ethyl acetate, washed with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=50/1) to obtain 16.9 mg of (2RS,4S,5S)-5-{L-N-[(2R or S)-5-ethylthio-2-(1-naphthylmethyl)pentanoyl]norleucyl}amino-2-ethyl-4-hydroxy-7-methyloctanoic acid isobutylamide as colorless solid.

후처리

  1. stirringThe mixture was stirred at the same temperature for one hour
  2. customat 5° C.
  3. customovernight
  4. washwashed with water and with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=50/1)

출처 및 근거

ORD 기록
ord-b6084522f7014ffaa529682d1bee6a84
출처 데이터셋
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05481036

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