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Nitrogen → 3'-((2-Cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)-6-methylbiphenyl-3-carboxylic acid

HRID 404969
ノート
印刷プレビュー

反応式

HRID 404969 の反応式
[CH:1]1([N:6]2[C:10](=[O:11])[C:9]3[CH:12]=[CH:13][C:14]([O:16][CH2:17][C:18]4[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=4)=[CH:15][C:8]=3[S:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.I[C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[CH3:37])[C:31]([OH:33])=[O:32].C([O-])([O-])=O.[Na+].[Na+].N#N>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH:1]1([N:6]2[C:10](=[O:11])[C:9]3[CH:12]=[CH:13][C:14]([O:16][CH2:17][C:18]4[CH:19]=[C:20]([C:28]5[C:36]([CH3:37])=[CH:35][CH:34]=[C:30]([C:31]([OH:33])=[O:32])[CH:29]=5)[CH:21]=[CH:22][CH:23]=4)=[CH:15][C:8]=3[S:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 6216403-Iodo-4-methylbenzoic acidHCID 667996663-((2-Cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)phenylboronic acid

生成物 1

HCID 533906803'-((2-Cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)-6-methylbiphenyl-3-carboxylic acid収率 36%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 3-((2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)phenylboronic acid (0.050 g, 0.14 mmol), 3-iodo-4-methylbenzoic acid (0.053 g, 0.20 mmol) and tetrakistriphenylphosphinepalladium(0) (0.016 mg, 0.014 mmol) were taken 2 mL of DME. To this 1M Na2CO3 (0.48 mmol) solution was added and the resulting solution was refluxed in an atmosphere of N2 for 12 h. The reaction mixture cooled to room temperature and the solvent was removed under vacuum. The solvent was evaporated and the residue was dissolved in water and neutralized using 1M HCl. The aqueous layer was extracted with ethyl acetate and the organic layer was dried over anhydrous Na2SO4. The solvent was evaporated in vacuum to obtain the crude acid as a yellow solid. The crude residue was purified using automated prep-HPLC to yield the desired compound as a pale yellow solid (0.023 g, 36%). 1H NMR (400 MHz, CDCl3): δ 8.01 (s, 1H), 7.90 (d, 1H, J=8.5 Hz), 7.65-7.23 (m, 7H), 7.03 (s, 1H), 5.23 (s, 2H), 4.64-4.59 (m, 1H), 2.34 (s, 3H), 2.16-2.14 (m, 2H), 1.88-1.68 (m, 6H). LC-MS (ESI) Calcd for C27H25NO4S [M+H]+: 460.15. Found: 460.00.

後処理

  1. customthe solvent was removed under vacuum
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous Na2SO4
  6. customThe solvent was evaporated in vacuum
  7. customto obtain the crude acid as a yellow solid
  8. customThe crude residue was purified

出典と根拠

ORDレコード
ord-2aa38b175e5145718420e06eeb9e5d9f
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08748632B2

反応ノート

読み込み中…

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