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Hydrochloric Acid → N2 (t-Butyloxycarbonyl)-O-(methylsulfonyl)-N-(phenylmethoxy)-L-threonineamid

HRID 2165275
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2165275
[N:1]#[N:2].[C:3]([O:7][C:8]([NH:10][C@H:11]([C:15]([NH:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[C@@H:12]([CH3:14])[OH:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:26][S:27](Cl)(=[O:29])=[O:28].Cl>N1C=CC=CC=1>[N:1]#[N:2].[C:3]([O:7][C:8]([NH:10][C@H:11]([C:15]([NH:17][O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:16])[C@@H:12]([CH3:14])[O:13][S:27]([CH3:26])(=[O:29])=[O:28])=[O:9])([CH3:4])([CH3:5])[CH3:6]
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Komponenten

5

Edukt 3

HCID 313Hydrochloric Acid2×HCID 31297Methanesulfonyl chlorideHCID 86744084N2 (t Butyloxycarbonyl)-N-(Phenylmethoxy)-L-threonineamide

Produkt 1

HCID 86744082N2 (t-Butyloxycarbonyl)-O-(methylsulfonyl)-N-(phenylmethoxy)-L-threonineamid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N2 -(t Butyloxycarbonyl)-N-(Phenylmethoxy)-L-threonineamide (244 g) was dissolved in 1.2 liters of pyridine and the solution was cooled to 0° C. With stirring 120 grams of methanesulfonyl chloride was added dropwise at 0°-5° C. After 2.5 hours, the reaction mixture was poured into a mixture of 1500 ml of 2N hydrochloric acid and ice and concentrated HCl was added to adjust the pH of the mixture to 4. The title compound crystallized, and, after stirring for 1 hour, was filtered off, washed with water and petroleum ether. After drying at room temperature the yield was 356.4 grams, which contained a considerable amount of water, melting point 128°-130° C. dec.

Aufarbeitung

  1. additionwas added dropwise at 0°-5° C
  2. additionwas added
  3. customThe title compound crystallized
  4. filtrationwas filtered off
  5. washwashed with water and petroleum ether
  6. customAfter drying at room temperature the yield was 356.4 grams, which

Quellen und Nachweise

ORD-Eintrag
ord-c89acd800449493fa6d216845b4402ad
Quelldatensatz
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04939253

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