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Lithium Hydroxide → (R)-3-(2-Chloro-N-isobutylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acid

HRID 1193288
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HRID 1193288 반응식
[Li+].[OH-].[Cl:3][C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[C:6]([N:8]([C@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([O:24]C)=[O:23])[CH:20]=2)[CH2:15][CH2:14]1)[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7]>O.CO.C1COCC1>[Cl:3][C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[C:6]([N:8]([C@H:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([OH:24])=[O:23])[CH:20]=2)[CH2:15][CH2:14]1)[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:7]
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참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 66799128(R)-Methyl 3-(2-chloro-N-isobutylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate

생성물 1

HCID 66798968(R)-3-(2-Chloro-N-isobutylbenzamido)-2,3-dihydro-1H-indene-5-carboxylic acid수율 78%

시약·촉매·용매 2

HCID 962Water용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

LiOH (173 mg, 4.156 mmol, 2 eq), dissolved in water (12 ml), was added dropwise to an ice-cooled (0° C.) solution of (R)-methyl 3-(2-chloro-N-isobutylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate (B-29) (0.8 g, 2.078 mmol, 1 eq) in MeOH:THF (1:1, 24 ml), and stirring was carried out for 8 h at RT. After monitoring by thin-layer chromatography, the reaction solution was concentrated and the residue was taken up in water (30 ml) and extracted with ethyl acetate (25 ml). The aqueous phase was adjusted to pH 3 with 2 M HCl and extracted with ethyl acetate (2×50 ml). The combined organic phases were washed with sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated under reduced pressure. Yield: 78% (600 mg, 1.62 mmol).

후처리

  1. concentrationthe reaction solution was concentrated
  2. extractionextracted with ethyl acetate (25 ml)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. washThe combined organic phases were washed with sat. NaCl solution (50 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4600169c7cef469dae6df57acae665f3
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08680159B2

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