Triethylamine → (3S)-3-{2-[(Methanesulfonyl)oxy]ethoxy}-4-(triphenylmethoxy)butyl methanesulfonate

HRID 863603ノート

反応式

HRID 863603 の反応式
[OH:1][CH2:2][CH2:3][O:4][C@H:5]([CH2:9][O:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH2:7][OH:8].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl>[CH3:37][S:38]([O:8][CH2:7][CH2:6][C@H:5]([O:4][CH2:3][CH2:2][O:1][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:9][O:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:40])=[O:39]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10786707(S)-3-(2-hydroxyethoxy)-4-trityloxybutanol

生成物 1

HCID 10209387(3S)-3-{2-[(Methanesulfonyl)oxy]ethoxy}-4-(triphenylmethoxy)butyl methanesulfonate収率 88.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

(S)-3-(2-hydroxyethoxy)-4-(tripenylmethoxy)-1-butanol (500 g, 1.27 mole) was dissolved in 4.8 L of CH2Cl2, was cooled to 0° C. under N2, and triethylamine (386.4 g, 532 mL, 3.81 mole, 3.0 eq.) was added. Methanesulfonyl chloride (396.3 g, 268 mL, 3.46 mole, 2.7 eq.) was then added dropwise over 30 minutes at <5° C. The resultant reaction mixture was stirred at 0° to 5° C. for 1-2 hours and was monitored by HPLC. The reaction mixture was diluted with additional CH2Cl2 and was washed twice with 2 L of water and 2 L of an aqueous saturated solution of ammonium chloride. The aqueous layers were back-extracted with 1 L of CH2Cl2 and the combined organic layer was dried (MgSO4) and evaporated in vacuo to give a crude solid that was recrystallized from 1/1 heptane/ethyl acetate to give 615 g (88%) of (S)-3-[2-[(methylsulfonyl)oxy]ethoxy]-4-(triphenylmethoxy)-1-butanol methane sulfonate in three crops as a solid. NMR. MS.

後処理

  1. customThe resultant reaction mixture
  2. washwas washed twice with 2 L of water and 2 L of an aqueous saturated solution of ammonium chloride
  3. extractionThe aqueous layers were back-extracted with 1 L of CH2Cl2
  4. dry with materialthe combined organic layer was dried (MgSO4)
  5. customevaporated in vacuo
  6. customto give a crude solid that
  7. customwas recrystallized from 1/1 heptane/ethyl acetate

出典と根拠

ORDレコード
ord-b2a7be3447c545288e2782be49a72e91
出典データセット
uspto-grants-1998_02
特許番号
US05721272

反応ノート

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