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

HRID 977284ノート

反応式

HRID 977284 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b08f4d519b1d4390a4c00a9d48497241
出典データセット
uspto-grants-1997_03
特許番号
US05614548

反応ノート

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