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Acetyl chloride → 1-Acetoxy-3-(benzyloxycarbonylamino)propane

HRID 64932
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 64932
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][OH:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[C:23]([O:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])(=[O:25])[CH3:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 562256Benzyl N-(3-hydroxypropyl)carbamate

Produkt 1

HCID 202357821-Acetoxy-3-(benzyloxycarbonylamino)propaneAusbeute 111 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In 200 ml of methylene chloride was dissolved 21 g of the 3-(benzyloxycarbonylamino)propanol, and 11 g of triethylamine was added thereto, after which 8.6 g of acetyl chloride was added thereto dropwise at -10° C. to -5° C. The resulting mixture was subjected to reaction at the same temperature for 1 hour. Subsequently, at room temperature, the reaction mixture was washed successively with 50 ml of diluted hydrochloric acid, 50 ml of a saturated aqueous sodium hydrogencarbonate solution and 50 ml of water, and then dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure to obtain 28 g of oily 1-acetoxy-3-(benzyloxycarbonylamino)propane.

Aufarbeitung

  1. additionwas added
  2. customdropwise at -10° C. to -5° C
  3. customThe resulting mixture was subjected to reaction at the same temperature for 1 hour
  4. washSubsequently, at room temperature, the reaction mixture was washed successively with 50 ml of diluted hydrochloric acid, 50 ml of a saturated aqueous sodium hydrogencarbonate solution and 50 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter which the solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1ead32642c024c7184a3d3b0a0c4f39d
Quelldatensatz
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04610983

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