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Potassium Carbonate → 2-(Trimethylsilyl)ethyl 3-(1-hydroxycyclohexyl)-2-(tosylamino)propylmethylcarbamate

HRID 2355438
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2355438
[CH3:1][NH:2][CH2:3][CH:4]([NH:13][S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:5][C:6]1([OH:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C([O-])([O-])=O.[K+].[K+].[C:30]([O:39]N1C(=O)CCC1=O)([O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=O>C1COCC1.O>[OH:12][C:6]1([CH2:5][CH:4]([NH:13][S:14]([C:17]2[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:3][N:2]([CH3:1])[C:30](=[O:39])[O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:37])[CH3:38])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 593830731-(3-(Methylamino)-2-(tosylamino)propyl)cyclohexanol

Produkt 1

HCID 671912342-(Trimethylsilyl)ethyl 3-(1-hydroxycyclohexyl)-2-(tosylamino)propylmethylcarbamateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883
Oxolane--water (1/1)
Lösungsmittel

Versuchsvorschrift

To a solution of 1-(3-(methylamino)-2-(tosylamino)propyl)cyclohexanol in 3:1 THF/H2O v/v (4 mL) was added K2CO3 (240 mg, 1.74 mmol), followed by Teoc-OSu (248 mg, 0.96 mmol). The resulting solution was stirred at rt for 30 min and the organic solvent was removed under reduced pressure. The residue was extracted with EtOAc (2×). The combined organic phases were washed with brine, dried, filtered and concentrated under vacuum. The residue was chromatographied on silica gel to give 2-(trimethylsilyl)ethyl 3-(1-hydroxycyclohexyl)-2-(tosylamino)propylmethylcarbamate (300 mg, 74% for two steps). MS m/z 469 (M+H+).

Aufarbeitung

  1. customthe organic solvent was removed under reduced pressure
  2. extractionThe residue was extracted with EtOAc (2×)
  3. washThe combined organic phases were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7a455da6d1fe403b82d1c04362d18df3
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07754737B2

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