4-Toluenesulfonyl chloride → (3S,5R)-5-Methyl-3-(toluene-4-sulfonyloxymethyl)nonanoic acid tert-butyl ester

HRID 722873노트

반응식

HRID 722873 반응식
[C:1]([O:5][C:6](=[O:18])[CH2:7][C@@H:8]([CH2:16][OH:17])[CH2:9][C@H:10]([CH3:15])[CH2:11][CH2:12][CH2:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:18])[CH2:7][C@@H:8]([CH2:16][O:17][S:25]([C:22]1[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=1)(=[O:27])=[O:26])[CH2:9][C@H:10]([CH3:15])[CH2:11][CH2:12][CH2:13][CH3:14])([CH3:3])([CH3:2])[CH3:4]

참가 물질

6

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 57065055(3S,5R)-3-Hydroxymethyl-5-methyl-nonanoic Acid Tert-butyl Ester

생성물 1

HCID 57230188(3S,5R)-5-Methyl-3-(toluene-4-sulfonyloxymethyl)nonanoic acid tert-butyl ester

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To alcohol 140 (6.14 mmol) in 30 mL CH2Cl2 at 0° C. was added DMAP (0.1 g), p-toluenesulfonyl chloride (1.37 g, 7.2 mmol), and then triethylamine (1.8 mL, 13 mmol) was added quickly dropwise. The mixture was warmed immediately to ambient temperature following addition and stirred overnight, and did not proceed to completion. The mixture was partitioned between Et2O and 1N HCl (aq), the phases were separated, and the organic phase washed with sat. NaHCO3 (aq), dried (MgSO4), and concentrated to provide tosylate 141. The product was used without further purification.

후처리

  1. additionaddition
  2. customThe mixture was partitioned between Et2O and 1N HCl (aq)
  3. customthe phases were separated
  4. washthe organic phase washed with sat. NaHCO3 (aq)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9c82a52cbcd542b7bc8f26f94a0cd1e6
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138542B2

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