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Dimethylformamide → Dimethylsulfamic acid 5-tert-butyl-4-{4-hydroxy-6,6-bis-[2-(4-hydroxyphenyl)ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methylphenyl ester

HRID 1003911
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1003911
[C:1]([C:5]1[CH:10]=[C:9]([O:11][S:12](=[O:17])(=[O:16])[NH:13][CH2:14][CH3:15])[C:8]([CH3:18])=[CH:7][C:6]=1[S:19]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:4])([CH3:3])[CH3:2].[OH:30][C:31]1[CH2:32][C:33]([CH2:50][CH2:51][C:52]2[CH:57]=[CH:56][C:55]([NH:58]C(=O)[O-])=[CH:54][CH:53]=2)([CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([NH:46]C(=O)[O-])=[CH:42][CH:41]=2)[O:34][C:35](=[O:37])[CH:36]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>CCOC(C)=O>[C:1]([C:5]1[C:6]([S:19][C:36]2[C:35](=[O:37])[O:34][C:33]([CH2:38][CH2:39][C:40]3[CH:41]=[CH:42][C:43]([NH2:46])=[CH:44][CH:45]=3)([CH2:50][CH2:51][C:52]3[CH:53]=[CH:54][C:55]([NH2:58])=[CH:56][CH:57]=3)[CH2:32][C:31]=2[OH:30])=[CH:7][C:8]([CH3:18])=[C:9]([O:11][S:12](=[O:16])(=[O:17])[NH:13][CH2:14][CH3:15])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]
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Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 10551814toluene-4-thiosulfonic acid S-(2-tert-butyl-4-ethylsulfamoyloxy-5-methyl-phenyl) esterHCID 86753329(3,6-dihydro-4-hydroxy-6-oxo-2H-pyran-2,2-diyl)bis[2, 1-ethanediyl-(4,1-phenylene)]biscarbamate

Produkt 1

HCID 54713187
Dimethylsulfamic acid 5-tert-butyl-4-{4-hydroxy-6,6-bis-[2-(4-hydroxyphenyl)ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methylphenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a round bottom flask equipped with a magnetic stirrer were added toluene-4-thiosulfonic acid S-(2-tert-butyl-4-ethylsulfamoyloxy-5-methyl-phenyl) ester (prepared in Example VVV; 0.218 g, 0.470 mmol), (1,1-dimethylethyl)[(3,6-dihydro-4-hydroxy-6-oxo-2H-pyran-2,2-diyl)bis[2,1-ethanediyl-(4, 1 -phenylene)]-biscarbamate (prepared in Example OO; 0.200 g, 0.380 mmol), K2CO3 (0.260 g, 1.88 mmol), and DMF (8 mL), as described in General Method 9. The reaction was stirred at room temperature for 3 hours and then worked up in the usual fashion. The residue was submitted to flash chromatography (100% EtOAc). The product form chromatography was taken up in EtOAc, triturated with hexane, filtered, and then taken up in CH2Cl2 (20 mL). Gaseous HCl was bubbled into this solution for 30 minutes. The solids that formed were filtered, washed with Et2O and dried under high vacuum to yield the title compound, m.p. 194° C. 1H NMR (DMSO-d6) δ 1.14 (t, 3 H), 1.49 (s, 9 H), 1.88 (s, 3 H), 2.09 (br m, 4 H), 2.70 (br m, 4 H), 3.12 (s, 2 H) 3.13 (m, 2 H), 6.79 (s, 1 H), 7.11 (s, 1 H), 7.27 (d, 4 H), 7.33 (d, 4 H), 8.40 (t, 1 H).

Aufarbeitung

  1. customTo a round bottom flask equipped with a magnetic stirrer
  2. customtriturated with hexane
  3. filtrationfiltered
  4. customGaseous HCl was bubbled into this solution for 30 minutes
  5. customThe solids that formed
  6. filtrationwere filtered
  7. washwashed with Et2O
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e761953179d04fd8b58b251b55662002
Quelldatensatz
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06046355

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