Ethyl Acetate → (2S, 6RS)-4-(4-chloro-quinolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

HRID 1432908노트

반응식

HRID 1432908 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH:16]([CH3:17])[CH2:15][NH:14][C:13](=[O:18])[C@@H:12]1[CH3:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([Cl:34])=[CH:29][CH:30]=[N:31]2)=[CH:26][CH:25]=1.C(OCC)(=O)C>C1COCC1.CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH:16]([CH3:17])[CH2:15][N:14]([CH2:23][C:24]2[CH:33]=[C:32]3[C:27]([C:28]([Cl:34])=[CH:29][CH:30]=[N:31]3)=[CH:26][CH:25]=2)[C:13](=[O:18])[C@@H:12]1[CH3:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 217084447-Bromomethyl-4-chloroquinolineHCID 57066025(2S,6RS)-2,6-Dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

생성물 1

HCID 57069199(2S, 6RS)-4-(4-chloro-quinolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester수율 95.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

(2S,6RS)-2,6-Dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (380 mg, 1.45 mmol) is dissolved in 10 mL of THF and 1 mL of DMF. Sodium hydride (60%, 72 mg, 3.14 mmol) is added at 0° C. and left to stir at room temperature for thirty minutes before 7-bromomethyl-4-chloro-quinoline (257 mg, 1.0 mmol) is added. The reaction is stirred for four hours. Ethyl acetate is added to the mixture, and the reaction is quenched with 3 mL of H2O. The two layers are separated and ethyl acetate (2×30 ml) is used to extract before dried over magnesium sulfate. The residue after filtration and concentration is chromatographed on silica gel (60% EtOAc/Hexane) to give (2S, 6RS)-4-(4-chloro-quinolin-7-ylmethyl)-2,6-dimethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (417 mg, 95% yield). C22H20ClN3O3 MS m/z: 438, 440.

후처리

  1. waitleft
  2. additionis added
  3. customthe reaction is quenched with 3 mL of H2O
  4. customThe two layers are separated
  5. extractionto extract
  6. dry with materialbefore dried over magnesium sulfate
  7. filtrationThe residue after filtration and concentration
  8. customis chromatographed on silica gel (60% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-ce0dc56101e6415d9fcf59d7ead7b5d2
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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