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Diethyl Ether → 2-(2-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-oxoethoxy)-5-chlorobenzoic acid

HRID 480181
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HRID 480181 반응식
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:12][C:13]([N:15]1[CH2:20][C@H:19]([CH3:21])[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:17][C@H:16]1[CH3:30])=[O:14].O.[OH-].[Li+].C(OCC)C>O1CCCC1.CO.O.ClCCl>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([O:11][CH2:12][C:13]([N:15]2[CH2:20][C@H:19]([CH3:21])[N:18]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[CH2:17][C@H:16]2[CH3:30])=[O:14])=[C:4]([CH:9]=1)[C:3]([OH:31])=[O:2]
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참가 물질

8

반응물 3

HCID 3283Diethyl EtherHCID 168937Lithium hydroxide, monohydrateHCID 11487716rel-Methyl 5-chloro-2-[2-[(2R,5S)-4-[(4-fluorophenyl)methyl]-2,5-dimethyl-1-piperazinyl]-2-oxoethoxy]benzoate

생성물 1

HCID 111664342-(2-((2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl)-2-oxoethoxy)-5-chlorobenzoic acid수율 35%

시약·촉매·용매 4

HCID 887
Methanol
용매
HCID 962Water용매
HCID 6344Dichloromethane용매
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2R, 5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzoic acid methyl ester (4.12 g, 9.18 mmol) in tetrahydrofuran (10 ml), methanol (10 ml) and water (4 ml) was added lithium hydroxide monohydrate (1.93 g, 45.9 mmol). The resulting mixture was stirred overnight at ambient temperature. The reaction was then concentrated, diluted with 1N hydrochloric acid and extracted with dichloromethane (2×). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated to give a white foam. Triteration in dichloromethane and diethyl ether gave the title compound (1.38 g, 35% yield).

후처리

  1. concentrationThe reaction was then concentrated
  2. additiondiluted with 1N hydrochloric acid
  3. extractionextracted with dichloromethane (2×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a white foam

출처 및 근거

ORD 기록
ord-18c818dae80843adad35ee74a9ee10be
출처 데이터셋
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06649611B2

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