Pyridine, hydrofluoride (1:1) → HCID 69274294, compound

HRID 749300Notes

Reaction equation

HRID 749300 reaction equation
N1C=CC=CC=1.[FH:7].[CH2:8]([CH:15]1[CH2:17][N@@:16]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[F:7][C@H:15]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:17][NH:16][S:18]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19]

Participants

3

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 178427308HCID 178427308, compound

Product 1

HCID 69274294HCID 69274294, compound

Procedure

To a stirred solution of hydrogen fluoride-pyridine (13 mL) at 0° C. under nitrogen was added (S)-(+)-2-benzyl-1-(p-tolylsulfonyl)aziridine (2 g) in one portion. The cooling bath was removed briefly until reaction became exothermic and then returned. After an additional 5 min. the reaction mixture was poured onto 100 mL of cracked ice. The product was extracted into ether, washed carefully with saturated NaHCO3 and brine, dried over Na2SO4, and evaporated to a white solid. The solid was triturated with hexane, collected and washed with ether/hexane to give 1.7 g of the title compound. Mp 130-133° C.; MS ES (M++H)=308.

Workup

  1. customThe cooling bath was removed briefly until reaction
  2. additionAfter an additional 5 min. the reaction mixture was poured onto 100 mL of cracked ice
  3. extractionThe product was extracted into ether
  4. washwashed carefully with saturated NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to a white solid
  7. customThe solid was triturated with hexane
  8. customcollected
  9. washwashed with ether/hexane

Sources & evidence

ORD record
ord-ea2b9278fe224b50a887025257c518e7
Source dataset
uspto-grants-2008_07
Patent number
US07402604B2

Reaction notes

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