(Diethylamino)sulfur trifluoride → HCID 18647601, compound

HRID 1682177Notes

Reaction equation

HRID 1682177 reaction equation
[Si]([O:8][C@@H:9]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C@H:11]([C@@H:12](O)[C:13](=[O:36])[C@@H:14]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:35])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:10]1)(C(C)(C)C)(C)C.C(N(S(F)(F)[F:44])CC)C>C(Cl)Cl>[OH:8][C@@H:9]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C@H:11]([C@@H:12]([F:44])[C:13](=[O:36])[C@@H:14]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:35])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C@H:19]([CH3:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:10]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 18647602HCID 18647602, compound

Product 1

HCID 18647601HCID 18647601, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 3α-tert-butyldimethylsilyloxy-6α-hydroxy-7-keto-5β-cholanoate (2.4 g, 4.49 mmoles) in methylene chloride (50 ml) was added dropwise in one hour to a solution of diethylamino-sulfur-trifluoride (2.72 ml, 20.0 mmoles) in methylene chloride (50 ml) and the mixture was left to react overnight under argon atmosphere, with magnetic stirring. The reaction mixture was washed with water (1×30 ml), subsequently with a sodium bicarbonate saturated solution (2×20 ml), finally with brine (1×30 ml). The organic phase was dried over sodium sulfate and concentrated under vacuum. The residue (2.0 g) was subjected to flash chromatography on silica, eluting with methylene chloride, to obtain 0.6 g of a pure product (32%).

Workup

  1. waitthe mixture was left
  2. customto react overnight under argon atmosphere, with magnetic stirring
  3. washThe reaction mixture was washed with water (1×30 ml), subsequently with a sodium bicarbonate saturated solution (2×20 ml), finally with brine (1×30 ml)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. washeluting with methylene chloride

Sources & evidence

ORD record
ord-5f09d50e5c7441c9b5876716e6bce46d
Source dataset
uspto-grants-1992_12
Patent number
US05175320

Reaction notes

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