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

HRID 1953385
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1953385
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

HCID 10209387(3S)-3-{2-[(Methanesulfonyl)oxy]ethoxy}-4-(triphenylmethoxy)butyl methanesulfonateAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(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 2L 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.

Aufarbeitung

  1. customThe resultant reaction mixture
  2. washwas washed twice with 2 L of water and 2L 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

Quellen und Nachweise

ORD-Eintrag
ord-3b4e4bc1e13746c4908f077b4cdcac6e
Quelldatensatz
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06117861

Notizen zur Reaktion

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