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2,2-Dimethoxypropane → HCID 15550447, Verbindung

HRID 1700831
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1700831
[OH:1][C@@H:2]1[C@H:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:4][C:3]1=[O:12].[CH3:13][O:14][C:15](OC)([CH3:17])[CH3:16].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CN(C)C=O>[CH3:13][O:14][C:15]([CH3:17])([O:1][C@@H:2]1[C@H:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:4][C:3]1=[O:12])[CH3:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10219589(3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone

Produkt 1

HCID 15550447HCID 15550447, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of the title product of step (a) of Example 1 (79.7 mg, 0.488 mmoles), dimethoxy propane (0.3 ml, 2.44 mmol), PPTS (about 12 mg, 0.049 mmol) and dimethylformamide (2 ml) under argon were stirred for 3 hours at about 0° C. and then for 24 hours at about 4° C. The product obtained was extracted with ethyl acetate and worked up (diluted with 10 ml ethyl acetate, washed with 0.5 saturated aqueous NaHCO3; aqueous fraction extracted with 2×5 ml ethyl acetate; combined organic fractions were washed with 1×10 ml water, 10 ml saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated) to obtain quantitive yield of products, which was a 1:1.7 mixture of starting material and the title product (determined by TLC analysis).

Aufarbeitung

  1. waitfor 24 hours at about 4° C
  2. customThe product obtained
  3. extractionwas extracted with ethyl acetate
  4. addition(diluted with 10 ml ethyl acetate, washed with 0.5 saturated aqueous NaHCO3; aqueous fraction extracted with 2×5 ml ethyl acetate; combined organic fractions were washed with 1×10 ml water, 10 ml saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated)
  5. customto obtain quantitive yield of products, which
  6. additiona 1:1.7 mixture of starting material

Quellen und Nachweise

ORD-Eintrag
ord-7e7f03164c524f949035c6a22308087a
Quelldatensatz
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06350886B1

Notizen zur Reaktion

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