5,5,6,6-Tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide → 3-[(1S)-3-hydroxy-1-[(5,5,6,6-tetramethyl-4,4-dioxo-1,4,3-oxathiazin-2-yl)amino]propyl]benzonitrile

HRID 539608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539608
[CH3:1][C:2]1([CH3:22])[C:7]([CH3:9])([CH3:8])[O:6][C:5](OC2C=CC([N+]([O-])=O)=CC=2)=[N:4][S:3]1(=[O:21])=[O:20].Cl.[NH2:24][C@H:25]([C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[C:32]#[N:33])[CH2:26][CH2:27][OH:28]>ClCCl.C(N(CC)C(C)C)(C)C>[OH:28][CH2:27][CH2:26][C@@H:25]([C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[C:32]#[N:33])[NH:24][C:5]1[O:6][C:7]([CH3:8])([CH3:9])[C:2]([CH3:1])([CH3:22])[S:3](=[O:20])(=[O:21])[N:4]=1

Komponenten

5

Edukt 2

HCID 718136815,5,6,6-Tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxideHCID 867054533-((S)-1-amino-3-hydroxypropyl)benzonitrile hydrochloride

Produkt 1

HCID 1784316813-[(1S)-3-hydroxy-1-[(5,5,6,6-tetramethyl-4,4-dioxo-1,4,3-oxathiazin-2-yl)amino]propyl]benzonitrileAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

100 mg of 5,5,6,6-tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 97 mg of 3-((S)-1-amino-3-hydroxypropyl)benzonitrile hydrochloride were dissolved in 5 ml of dichloromethane and 0.25 ml of N,N-diisopropylethylamine, and the mixture was stirred at room temperature for 16 hours. Subsequently, the reaction solution was diluted with 20 ml of dichloromethane, and washed with 10 ml of 10% aqueous ammonia solution and with 10 ml of 1 N aqueous hydrochloric acid. The two aqueous phases were extracted once again with 20 ml of ethyl acetate, and the combined organic phases were dried over Na2SO4 and concentrated by rotary evaporation. The residue was purified in a purification laboratory by means of preparative HPLC. After lyophilization of the product-containing fractions, the product (66 mg) was thus obtained with a molecular weight of 365.5 g/mol (C17H23N3O4S); MS (ESI): m/e=366 (M+H+).

Aufarbeitung

  1. washwashed with 10 ml of 10% aqueous ammonia solution and with 10 ml of 1 N aqueous hydrochloric acid
  2. extractionThe two aqueous phases were extracted once again with 20 ml of ethyl acetate
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified in a purification laboratory by means of preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f1293230b438472581beb4e44c500720
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871758B2

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