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Pentachlorophenol → Ethyl ((benzyloxy)carbonyl)-L-phenylalanylglycinate

HRID 1580550
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인쇄 미리보기

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HRID 1580550 반응식
[C:1]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].ClC1C(O)=C(Cl)C(Cl)=C(Cl)C=1Cl.C([N+]#[C-])(C)C.Cl.[CH2:41]([O:43][C:44](=[O:47])[CH2:45][NH2:46])[CH3:42]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:41]([O:43][C:44](=[O:47])[CH2:45][NH:46][C:20](=[O:22])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH3:42]
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참가 물질

7

반응물 4

HCID 992PentachlorophenolHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 150783Isopropyl isocyanideHCID 2723640Glycine ethyl ester, hydrochloride

생성물 1

HCID 12628842Ethyl ((benzyloxy)carbonyl)-L-phenylalanylglycinate수율 82%

시약·촉매·용매 2

HCID 6212
Chloroform
용매
2회
HCID 8471Triethylamine용매

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온도
50 °C

실험 절차

A solution of 6.0 (20 mM) N-carbobenzoxy-L-phenylalanine, 5.3 g (20 mM) pentachlorophenol, and 2.0 g (30 mM) is isopropyl isonitrile in 40 ml chloroform was mixed with a solution of 2.8 g (20 mM) glycine ethyl ester hydrochloride and 2.02 g (20 mM) triethylamine in 30 ml chloroform. The mixture was heated at 50°C for 24 hours and evaporated. The residue was taken up in 150 ml ethyl acetate. The solution was washed sequentially with 100 ml water, 120 ml 1-N hydrochloric acid, four times 120 ml 5% sodium bicarbonate solution, and again with 100 ml water, then dried with desiccated sodium sulfate and evaporated. When the residue was crystallized from ethyl acetate and petroleum ether, 6.3 g N-carbobenzoxy-L-phenylalanyl-glycine ethyl ester was obtained (82 percent yield). Recrystallizing from ethyl acetate and petroleum ether reduced the yield to 5.4 g (70%). M.P. 107°-108.5°C. [ α]D25 = - 17.1° (C = 2, in ethanol).

후처리

  1. customevaporated
  2. washThe solution was washed sequentially with 100 ml water, 120 ml 1-N hydrochloric acid, four times 120 ml 5% sodium bicarbonate solution
  3. dry with materialagain with 100 ml water, then dried with desiccated sodium sulfate
  4. customevaporated
  5. customWhen the residue was crystallized from ethyl acetate and petroleum ether

출처 및 근거

ORD 기록
ord-89945cfb45ce4ab28282d1c7ff2ed7b2
출처 데이터셋
uspto-grants-1976_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US03933783

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