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Cesium carbonate → (1S,2S)-2-(4-{(R)-7-Fluoro-4-[4-(3-hydroxy-3-methyl-butoxy)-phenoxy]-indan-1-yloxy}-phenyl)-cyclopropanecarboxylic acid ethyl ester

HRID 625691
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HRID 625691 반응식
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([O:26][C:27]4[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=4)[CH:21]=[CH:22][C:23]=3[F:25])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2].[OH:34][C:35]([CH3:50])([CH3:49])[CH2:36][CH2:37]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:10]=[CH:11][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([O:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH2:37][CH2:36][C:35]([OH:34])([CH3:50])[CH3:49])=[CH:29][CH:28]=4)[CH:21]=[CH:22][C:23]=3[F:25])[CH2:18][CH2:17]2)=[CH:13][CH:14]=1)=[O:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol2회HCID 118093735(1S,2S)-2-{4-[(R)-7-Fluoro-4-(4-hydroxy-phenoxy)-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester2회

생성물 1

HCID 118093710(1S,2S)-2-(4-{(R)-7-Fluoro-4-[4-(3-hydroxy-3-methyl-butoxy)-phenoxy]-indan-1-yloxy}-phenyl)-cyclopropanecarboxylic acid ethyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

(1S,2S)-2-{4-[(R)-7-Fluoro-4-(4-hydroxy-phenoxy)-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester (Intermediate 7, 47 mg, 0.10 mmol), toluene-4-sulfonic acid 3-hydroxy-3-methyl-butyl ester (Intermediate 10, 54 mg, 0.21 mmol), and cesium carbonate (107 mg, 0.21 mmol) are suspended in dry N,N-dimethylformamide (2 mL) and stirred overnight. The mixture is diluted with ethyl acetate, washed with water, dried and the solvent removed. The residue is purified by flash chromatography (gradient of ethyl acetate in cyclohexane) to give the title compound. (Yield 60 mg). LC (METHOD 6): tR=0.75 min; Mass spectrum (ES+): m/z=535 [M+H]+.

후처리

  1. washwashed with water
  2. customdried
  3. customthe solvent removed
  4. customThe residue is purified by flash chromatography (gradient of ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-1332b1d936584c288a0a5d28458bd02f
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09308194B2

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