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Triethylamine → HCID 70094445, 화합물

HRID 1075638
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인쇄 미리보기

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HRID 1075638 반응식
[CH2:1]([O:8][C:9]([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:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:25](CC)CC)C.ClC(OCC)=O.N[C@@H:37]1[C:43](=[O:44])[N:42]2[C@@H:38]1[O:39][CH2:40][CH2:41]2>ClCCl.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([C@H:37]1[C:43](=[O:44])[N:42]2[C@@H:38]1[O:39][CH2:40][CH:41]2[NH2:25])=[O:22])[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 21309376HCID 21309376, 화합물

생성물 1

HCID 70094445HCID 70094445, 화합물수율 17%

시약·촉매·용매 2

HCID 6344Dichloromethane
용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
-2.5 °C

실험 절차

To a solution of N-benzyloxycarbonyl-L-phenylalanine (867 mg, 2.90 mmole) and triethylamine (323 mg, 3.2 mmole) in dichloromethane (20 ml), ethyl chloroformate (315 mg, 2.90 mmole) was added at -15° C. The reaction mixture was stirred at -10 to 5° C. for 1.5 hrs. Then a precooled (~-15° C.) solution of (5R,6S)-6-amino-4-oxa-1-azabicyclo[3,2,0]heptan-7-one in ethyl acetate (see above) was added at -15° C. and the resulting mixture was stirred at room temperature for 10 hrs. After removal of solvent, the residue was dissolved in ethyl acetate, washed with water, brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (55:45) as eluent and 205 mg of the title compound was obtained as white solid.

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 10 hrs
  2. customAfter removal of solvent
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of solvent
  7. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-d873c7354f284b6aba7483b857444abf
출처 데이터셋
uspto-grants-1999_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05905076

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