Lipoic acid → 2-(dimethylamino)ethyl (R)-5-(1,2-dithiolan-3-yl)pentanoate

HRID 520267

반응식

HRID 520267 반응식
C1CCC(N=C=NC2CCCCC2)CC1.[CH2:16]1[C@@H:20]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[S:19][S:18][CH2:17]1.[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31]O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[S:18]1[CH2:17][CH2:16][C@@H:20]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:31][CH2:30][N:29]([CH3:33])[CH3:28])=[O:26])[S:19]1

참가 물질

6

반응물 3

HCID 6112Lipoic acidHCID 79022-(Dimethylamino)ethanolHCID 10868Dicyclohexylcarbodiimide

생성물 1

HCID 154622652-(dimethylamino)ethyl (R)-5-(1,2-dithiolan-3-yl)pentanoate수율 79%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

A solution of DCC (11 g, 53 mmol) in anhydrous CH2Cl2 (20 mL) was added with stirring over 10-20 minutes to a cold (0° C.) solution of R-lipoic acid (10.0 g, 48.5 mmol), N,N-dimethylethanolamine (14.5 mL, 145 mmol, 3 eq.), and DMAP (600 mg, 4.9 mmol) in anhydrous CH2Cl2 (50 mL). Following complete addition, the cold bath was removed. After 18 hours at room temperature, all volatiles were removed under reduced pressure, and the resulting residue was purified by flash column chromatography (SiO2, 2% MeOH in CH2Cl2) providing the desired product as a clear yellow oil (10.6 g, 79%). All data consistent with values reported in the literature. (See Courvoisier C. et al. 2006. Synthesis and effects of 3-methylthiopropanoyl thiolesters of lipoic acid, methional metabolite mimics. Bioorganic Chemistry 34(1):49-58.)

후처리

  1. additionaddition
  2. customthe cold bath was removed
  3. customall volatiles were removed under reduced pressure
  4. customthe resulting residue was purified by flash column chromatography (SiO2, 2% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-bff83dd917164fbf97a103a606dd1f09
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326970B2

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