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 1426878노트

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HRID 1426878 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

HCID 86696599(R)-1-(5-tert-Butoxy-2-isopropoxy-benzothiazol-7-yl)-2-chloro-ethanol수율 102.2%

시약·촉매·용매 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)촉매HCID 21901440N,N-dimethylformamide methanol용매

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온도
30 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dff6560dbbbf44e88ae16739157bcf0d
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933108B2

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