Isopropyl isocyanate → N-(2-tetrahydropyranyloxy)-2-[4-isopropylcarbamoyl-7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide

HRID 1063923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1063923
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:36])[CH2:10][C:11]1([C:20]2[S:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[O:35][CH:34]=[N:33][CH:32]=4)=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[CH:37]([N:40]=[C:41]=[O:42])([CH3:39])[CH3:38]>C(Cl)(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:36])[CH2:10][C:11]1([C:20]2[S:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[O:35][CH:34]=[N:33][CH:32]=4)=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[S:17](=[O:18])(=[O:19])[CH2:16][CH2:15][N:14]([C:41](=[O:42])[NH:40][CH:37]([CH3:39])[CH3:38])[CH2:13][CH2:12]1

Komponenten

4

Edukt 2

HCID 61277Isopropyl isocyanateHCID 22276407N-(2-tetrahydropyranyloxy)-2-[7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide

Produkt 1

HCID 22276377N-(2-tetrahydropyranyloxy)-2-[4-isopropylcarbamoyl-7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamideAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a mixture of N-(2-tetrahydropyranyloxy)-2-[7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (100 mg) in chloroform (1 ml) was added a solution of isopropyl isocyanate (18 mg) in chloroform (1 ml) at 0° C. under nitrogen atmosphere. After being stirred for 1 hour, the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and the solution was washed with water, a saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform-methanol=10-1, v/v) to give N-(2-tetrahydropyranyloxy)-2-[4-isopropylcarbamoyl-7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (92 mg) as a pale yellow powder.

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed with water
  4. dry with materiala saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin-layer chromatography (chloroform-methanol=10-1

Quellen und Nachweise

ORD-Eintrag
ord-fecdce8d4f8d42cc859b345121562ae7
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967197B2

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