StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dichloromethane → tert-Butyl ((1S,2R)-1-benzyl-2-hydroxy-3-(isobutyl((4-nitrophenyl)sulfonyl)amino)propyl)carbamate

HRID 1505572
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1505572
[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@H:9]([OH:16])[CH2:10][NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)Cl.[N+:35]([C:38]1[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1)([O-:37])=[O:36]>O>[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C@H:9]([OH:16])[CH2:10][N:11]([S:44]([C:41]1[CH:40]=[CH:39][C:38]([N+:35]([O-:37])=[O:36])=[CH:43][CH:42]=1)(=[O:45])=[O:46])[CH2:12][CH:13]([CH3:14])[CH3:15])([CH3:3])([CH3:4])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 9902339tert-Butyl ((2S,3R)-3-hydroxy-4-((2-methylpropyl)amino)-1-phenylbutan-2-yl)carbamate

Produkt 1

HCID 10279676tert-Butyl ((1S,2R)-1-benzyl-2-hydroxy-3-(isobutyl((4-nitrophenyl)sulfonyl)amino)propyl)carbamateAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
42.5 °C

Versuchsvorschrift

[(1S,2R)-3-[(2-methylpropyl)amino]-2-hydroxy-1-(phenyl methyl)propyl]carbamic acid tert-butyl ester (4, 100 gm) and triethylamine (39.04 g) was added to methylenedichloride (1200 mL) and the temperature was raised to 40° C. p-nitro benzene sulfonyl chloride solution (72.3 g of p-NBSC dissolve in 300 mL methylenedichloride) was added slowly at 40-45° C. for 2-3 hrs. The reaction was maintained for 3 hours at 40-45° C. After completion of the reaction, water (500 mL) was added, separated the organic layer and distilled out methylene dichloride at atmospheric pressure. Finally, strip out the methylene dichloride by using isopropyl alcohol (200 mL). Isopropyl alcohol (1000 mL) was added to the distillate and maintained the stirring for 60 minutes at 70-80° C. Cooled the mass to 30-35° C., filtered and washed with Isopropyl alcohol to get title compound 3 (yield 145 g).

Aufarbeitung

  1. additionwas added slowly at 40-45° C. for 2-3 hrs
  2. additionwas added
  3. customseparated the organic layer
  4. distillationdistilled out methylene dichloride at atmospheric pressure
  5. additionIsopropyl alcohol (1000 mL) was added to the distillate
  6. temperaturemaintained the stirring for 60 minutes at 70-80° C
  7. temperatureCooled the mass to 30-35° C.
  8. filtrationfiltered
  9. washwashed with Isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-29f8020d0da140b6b0a79a4e1fb17dd9
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09216990B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion