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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
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 404969
[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
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Komponenten

7

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2aa38b175e5145718420e06eeb9e5d9f
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08748632B2

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