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

HRID 1829784Notes

Reaction equation

HRID 1829784 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. M.P. 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-ea4a41b55a5140f499acb30dd72c4b0b
Source dataset
uspto-grants-2006_06
Patent number
US07064143B1

Reaction notes

Loading…