1-(5-Tert-butoxy-2-isopropoxy-benzothiazol-7-yl)-2-chloro-ethanone → (R)-1-(5-tert-Butoxy-2-isopropoxy-benzothiazol-7-yl)-2-chloro-ethanol

HRID 1426878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426878
[C:1]([O:5][C:6]1[CH:7]=[C:8]([C:19](=[O:22])[CH2:20][Cl:21])[C:9]2[S:13][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[N:11][C:10]=2[CH:18]=1)([CH3:4])([CH3:3])[CH3:2]>CO.CN(C=O)C.CC1C=CC(C(C)C)=CC=1.CC1C=CC(S([N-][C@H]([C@@H](N)C2C=CC=CC=2)C2C=CC=CC=2)(=O)=O)=CC=1.Cl[Ru+]>[C:1]([O:5][C:6]1[CH:7]=[C:8]([C@@H:19]([OH:22])[CH2:20][Cl:21])[C:9]2[S:13][C:12]([O:14][CH:15]([CH3:16])[CH3:17])=[N:11][C:10]=2[CH:18]=1)([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 1

HCID 866965981-(5-Tert-butoxy-2-isopropoxy-benzothiazol-7-yl)-2-chloro-ethanone

Produkt 1

HCID 86696599(R)-1-(5-tert-Butoxy-2-isopropoxy-benzothiazol-7-yl)-2-chloro-ethanolAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11974997Chloridoruthenium(1+) [(1S,2S)-2-amino-1,2-diphenylethyl](4-methylbenzene-1-sulfonyl)azanide--1-methyl-4-(propan-2-yl)benzene (1/1/1)KatalysatorHCID 21901440N,N-dimethylformamide methanolLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

A suspension of 1-(5-tert-butoxy-2-isopropoxybenzo[d]thiazol-7-yl)-2-chloro-ethanone (70 g, 204.8 mmol) and RuCl(p-cymene)[(S,S)-Ts-DPEN] (1.954 g, 3.07 mmol) in methanol/DMF (1330 ml/70 ml) was degassed and refilled with N2 three times. A degassed preformed mixture of formic acid (28.3 g) in Et3N (124.3 g) was added slowly while keeping the internal temperature between 15 to 20° C. The resulting yellow suspension was warmed up to 30° C. After 2 h the reaction mixture is cooled to 25° C., water (750 ml) was then added into the reaction mixture followed by the addition of acetic acid (56 ml) in one portion. The mixture was concentrated and then diluted with TBME (1000 ml). Aqueous phase was separated and extracted with TBME (1000 ml). The combined organic phase was washed sequentially with water and brine and then dried with Na2SO4 and concentrated under vacuum to give (R)-1-(5-tert-Butoxy-2-isopropoxy-benzothiazol-7-yl)-2-chloro-ethanol (72 g).

Aufarbeitung

  1. customwas degassed
  2. additionrefilled with N2 three times
  3. additionmixture of formic acid (28.3 g) in Et3N (124.3 g)
  4. additionwas added slowly
  5. custombetween 15 to 20° C
  6. temperatureAfter 2 h the reaction mixture is cooled to 25° C.
  7. additionwater (750 ml) was then added into the reaction mixture
  8. additionfollowed by the addition of acetic acid (56 ml) in one portion
  9. concentrationThe mixture was concentrated
  10. additiondiluted with TBME (1000 ml)
  11. customAqueous phase was separated
  12. extractionextracted with TBME (1000 ml)
  13. washThe combined organic phase was washed sequentially with water and brine
  14. dry with materialdried with Na2SO4
  15. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-dff6560dbbbf44e88ae16739157bcf0d
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933108B2

Notizen zur Reaktion

Wird geladen…