Triethylamine → (+/-)-1-S-hexadecyl-2-O-methyl-3-O-mesylthioglycerol

HRID 977284노트

반응식

HRID 977284 반응식
[CH2:1]([S:17][CH2:18][CH:19]([CH2:22][OH:23])[O:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH2:1]([S:17][CH2:18][CH:19]([CH2:22][O:23][S:32]([CH3:31])(=[O:34])=[O:33])[O:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 145227763-(Hexadecylsulfanyl)-2-methoxypropan-1-OL

생성물 1

HCID 14522778(+/-)-1-S-hexadecyl-2-O-methyl-3-O-mesylthioglycerol수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3.0 grams (0.009 mole) (±)-1-S-hexadecyl-2-O-methylthioglycerol in 200 milliliters of DCM and 1.0 milliliter (0.010 mole) of triethylamine was added 1.2 grams (0.012 mole) of methanesulfonyl chloride and the reaction stirred at room temperature for 24 hours. The reaction mixture was then extracted twice with 200 milliliter portions of water, twice with 200 milliliter portions of 5% HCl, once with 200 milliliters of saturated NaHCO3, and once with 200 milliliters of brine. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to yield 3.4 grams (89%) of a colorless oily residue. 1H-NMR (CDCl3): delta, 0.87(t, 3H, terminal methyl), 1.2-1.6[m, 28H, (CH2)14 ], 2.58(m, 2H, S--CH2), 2.62(m, 2H, CH--CH2 --S), 3.08(s, 3H, SO2 --CH3), 3.40-3.50(m, 4H, CH, CH3 --O), 4.35 (m, 2H, CH2 --OSO2).

후처리

  1. extractionThe reaction mixture was then extracted twice with 200 milliliter portions of water, twice with 200 milliliter portions of 5% HCl, once with 200 milliliters of saturated NaHCO3
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-b08f4d519b1d4390a4c00a9d48497241
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05614548

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