Water → (+/-)-1,1-Dimethylethyl [1-[[[(4-methylphenyl)-sulfonyl]oxy]methyl]-2-methylpropyl]carbamate

HRID 1790004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1790004
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC([N:16]([CH:20]([CH2:24][OH:25])[CH:21]([CH3:23])[CH3:22])[C:17](=[O:19])[OH:18])(C)C.O>N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:25][CH2:24][CH:20]([NH:16][C:17](=[O:19])[O:18][C:2]([CH3:7])([CH3:3])[CH3:1])[CH:21]([CH3:22])[CH3:23])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 726838321,1-Dimethylethyl [1-(hydroxymethyl)-2-methylpropyl]carbamic acid

Produkt 1

HCID 14476730(+/-)-1,1-Dimethylethyl [1-[[[(4-methylphenyl)-sulfonyl]oxy]methyl]-2-methylpropyl]carbamateAusbeute 123,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

4-Methylbenzenesulfonyl chloride (0.2222 mol) was added portionwise at 10° C. to a mixture of 1,1-dimethylethyl [1-(hydroxymethyl)-2-methylpropyl]carbamic acid (ester) (0.202 mol) in pyridine (65 ml). The mixture was stirred at 10° C. for 2 hours. H2O (75 ml) was added at 10° C. The precipitate was filtered off, washed with H2O and taken up in CH2Cl2. The organic solution was washed with H2O, dried, filtered and the solvent was evaporated, yielding 49 g (68%) of (±)-1,1-dimethylethyl [1-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-2-methylpropyl]carbamate; mp. 85° C. (interm. 32).

Aufarbeitung

  1. filtrationThe precipitate was filtered off
  2. washwashed with H2O
  3. washThe organic solution was washed with H2O
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d01099ba7a7745ea9ec56d0be6ad390a
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071192B1

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