Allylamine → HCID 66726783, compound

HRID 1845944Notes

Reaction equation

HRID 1845944 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].CS(O[CH2:10][C@H:11]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24])(=[O:16])=[O:15])[CH3:12])(=O)=O>O1CCCC1>[CH2:1]([NH:4][CH2:12][C@H:11]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24])(=[O:16])=[O:15])[CH3:10])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 86661757HCID 86661757, compound

Product 1

HCID 66726783HCID 66726783, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

5.4 mL of allylamine was added to a tetrahydrofuran (100 mL) solution of 8.2 g of (R)-2-(2-nitrophenylsulfonamido)propyl methanesulfonate, and the mixture was stirred at 80° C. for 16 hours. After the completion of reaction, the reaction solution was returned to room temperature, and 100 mL of saturated saline was added thereto. From this mixed solution, two extractions were performed with 100 mL of ethyl acetate. The extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 7 g of the compound of interest as a yellow oil (96%).

Workup

  1. customAfter the completion of reaction
  2. customwas returned to room temperature
  3. addition100 mL of saturated saline was added
  4. extractionFrom this mixed solution, two extractions
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customthe obtained crude product
  9. customwas purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-d297c204e8924e7ba80a1970f88affdd
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

Loading…