Ammonia → benzyl 3-aminosulfonyl-2(R)-methylpropionate

HRID 8829Notes

Reaction equation

HRID 8829 reaction equation
Cl[S:2]([CH2:5][C@H:6]([CH3:17])[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(=[O:4])=[O:3].[NH3:18]>C(Cl)Cl.C(OCC)(=O)C>[NH2:18][S:2]([CH2:5][C@H:6]([CH3:17])[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 18738445HCID 18738445, compound

Product 1

HCID 18738444benzyl 3-aminosulfonyl-2(R)-methylpropionate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

A 100 mL round bottom flask equipped with magnetic stir bar was charged with 1.22 g of benzyl 3-chlorosulfonyl-2(R)-methylpropionate in 15 mL CH2Cl2 and cooled to −78° C. To this solution was added to 10 mL of liquid ammonia at −78° C. After 20 minutes the reaction was warmed to room temperature, concentrated in vacuo to afford a white solid. The solid was slurried in ethyl acetate, filtered to remove inorganic salts and concentrated in vacuo to afford 1.08 g of benzyl 3-aminosulfonyl-2(R)-methylpropionate as a clear yellow oil. The crude product was used without further purification.

Workup

  1. customA 100 mL round bottom flask equipped with magnetic stir bar
  2. temperatureAfter 20 minutes the reaction was warmed to room temperature
  3. concentrationconcentrated in vacuo
  4. customto afford a white solid
  5. filtrationfiltered
  6. customto remove inorganic salts
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d52e816d05f1498dbac26bd0c69dc46e
Source dataset
uspto-grants-2006_08
Patent number
US07091219B2

Reaction notes

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