Water → Arachidonyl methane sulfonate

HRID 1861238노트

반응식

HRID 1861238 반응식
[CH2:1]([OH:21])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH3:22][S:23](Cl)(=[O:25])=[O:24].O.CCOCC>N1C=CC=CC=1>[CH3:22][S:23]([O:21][CH2:1][CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])(=[O:25])=[O:24]

참가 물질

6

반응물 4

HCID 962WaterHCID 3283Diethyl EtherHCID 31297Methanesulfonyl chlorideHCID 10891603Arachidonyl alcohol

생성물 1

HCID 11122179Arachidonyl methane sulfonate수율 59%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

Arachidonyl alcohol (0.34 mmol, 100 mg) in dry pyridine (5 ml) was cooled to 0° C. Methane sulfonyl chloride (0.52 mmol; 40 mg) was added to the above solution under a nitrogen atmosphere. The reaction mixture was slowly brought to room temperature at which the reaction was continued for 5 hours. Water (20 ml) and ether (20 ml) were then added to the reaction mixture after which the organic phase was separated, washed with 2N sulfuric acid, then with water and then with a 10% solution of potassium carbonate. The reaction mixture was dried by evaporation of the solvents to obtain an the oily product arachidonyl methane sulfonate, (75 mg; yield 59%) exhibiting the following: 1H HMR (CDCl3) δ 5.34-5.41 (m, 8H), 4.23 (t, J=6.6 Hz, 2H), 3.00 (s, 3H), 2.75-2.84 (m, 6H), 2.04-2.12 (m, 4H), 1.65-1.74 (m, 2H), 1.33-1.50 (m, 2H), 1.25-.130 (m, 6H), 0.89 (t, J=7.2 Hz, 3H). IR (cm−1): 2900, 2850, 1350, 1170, 940.

후처리

  1. customwas slowly brought to room temperature at which
  2. customwas separated
  3. washwashed with 2N sulfuric acid
  4. customThe reaction mixture was dried by evaporation of the solvents

출처 및 근거

ORD 기록
ord-582dcfcb90bc4a83b34c174a5e26baf0
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531636B1

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