Triphenylphosphine → 1-Tert-butoxycarbonyl-4-(3-chlorophenyl)-2(s)-[2-(2-cyano-5-methoxycarbonylphenoxy)ethyl]-5-oxo-piperazine

HRID 379027노트

반응식

HRID 379027 반응식
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[OH:13])#[N:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:33]([O:37][C:38]([N:40]1[CH2:45][C:44](=[O:46])[N:43]([C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[CH:48]=2)[CH2:42][C@@H:41]1[CH2:54][CH2:55]O)=[O:39])([CH3:36])([CH3:35])[CH3:34].CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CCCCCC.CCOC(C)=O>[C:33]([O:37][C:38]([N:40]1[CH2:45][C:44](=[O:46])[N:43]([C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[CH:48]=2)[CH2:42][C@@H:41]1[CH2:54][CH2:55][O:13][C:4]1[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=[CH:12][C:3]=1[C:1]#[N:2])=[O:39])([CH3:36])([CH3:35])[CH3:34]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 16641129Methyl 4-cyano-3-hydroxybenzoateHCID 20691434(S)-4-(tert-butoxycarbonyl)-1-(3-chlorophenyl)-5-(2-hydroxyethyl)piperazin-2-one

생성물 1

HCID 206914331-Tert-butoxycarbonyl-4-(3-chlorophenyl)-2(s)-[2-(2-cyano-5-methoxycarbonylphenoxy)ethyl]-5-oxo-piperazine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 21226206Ethyl acetate hexane용매

실험 절차

To a solution of 250 mg of methyl 4-cyano-3-hydroxybenzoate (1.42 mmol), as described in Example 4, Step C, and PPh3 (465 mg, 1.77 mmol) in THF (10 mL) was added dropwise a solution of the alcohol from Step E above (503 mg, 1.42 mmol) and DEAD (0.28 mL, 1.77 mmol) in THF (5 mL). After stirring for 16 hr, the solution was concentrated in vacuo and the residue taken up in EtOAc. This was then washed with 10% citric acid solution, saturated NaHCO3 solution, brine and dried over MgSO4. Filtration and removal of the solvent afforded an oil. Column chromatography (silica gel; hexane:EtOAc 4:1) afforded the title compound as a clear oil.

후처리

  1. concentrationthe solution was concentrated in vacuo
  2. washThis was then washed with 10% citric acid solution, saturated NaHCO3 solution, brine
  3. dry with materialdried over MgSO4
  4. filtrationFiltration and removal of the solvent
  5. customafforded an oil

출처 및 근거

ORD 기록
ord-803ee359b31a40149f696cffb6d8027a
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297239B1

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