Lithium diisopropylamide → Dihydro-7-(2-acetylthioethyl)-1-pyrindine-6,6-bisphosphonic acid, tetraethyl ester

HRID 963641노트

반응식

HRID 963641 반응식
[NH:1]1[C:9]2[C:5](=[CH:6][C:7]([P:18]([O:23][CH2:24][CH3:25])(=[O:22])[O:19][CH2:20][CH3:21])([P:10]([O:15][CH2:16][CH3:17])(=[O:14])[O:11][CH2:12][CH3:13])[CH:8]=2)[CH:4]=[CH:3][CH2:2]1.C([N-]C(C)C)(C)C.[Li+].[C:34]([S:37][CH2:38][CH2:39]I)(=[O:36])[CH3:35]>C1COCC1>[C:34]([S:37][CH2:38][CH2:39][C:8]1[C:7]([P:18]([O:23][CH2:24][CH3:25])(=[O:22])[O:19][CH2:20][CH3:21])([P:10]([O:11][CH2:12][CH3:13])(=[O:14])[O:15][CH2:16][CH3:17])[CH:6]=[C:5]2[C:9]=1[NH:1][CH2:2][CH:3]=[CH:4]2)(=[O:36])[CH3:35]

참가 물질

5

반응물 3

HCID 2724682Lithium diisopropylamideHCID 190830772-Acetylthio-1-iodoethaneHCID 86752757Dihydro-1-pyrindine-6,6-diphosphonic acid tetraethyl ester

생성물 1

HCID 86752760Dihydro-7-(2-acetylthioethyl)-1-pyrindine-6,6-bisphosphonic acid, tetraethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a solution of dihydro-1-pyrindine-6,6-bisphosphonic acid, tetraethyl ester (7.0 mmol) [prepared as described in Example A, Part I] in anhydrous THF (100 ml) at -78° C. under argon is added dropwise a pregenerated solution of lithium diisopropyl amide (7.0 mmol) in THF (10 ml). After stirring 30 minutes, to this is added 2-acetylthio-1-iodoethane (7.5 mmol) in THF (25 ml). The reaction mixture is stirred at -78° C. for 5 hours then allowed to warm to room temperature and stirred overnight. The reaction is quenched by the addition of saturated aqueous ammonium chloride and then extracted with diethyl ether. The organic layers are combined, dried over sodium sulfate, filtered and concentrated under reduced pressure. The desired product is purified by flash chromatography using a 5-10% isopropanol in methylene chloride gradient on silica gel.

후처리

  1. stirringThe reaction mixture is stirred at -78° C. for 5 hours
  2. stirringstirred overnight
  3. customThe reaction is quenched by the addition of saturated aqueous ammonium chloride
  4. extractionextracted with diethyl ether
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe desired product is purified by flash chromatography

출처 및 근거

ORD 기록
ord-623e28d9728c475baea254e8982d4a02
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763611

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