Dimethylamine → HCID 18738447, compound

HRID 8831Notes

Reaction equation

HRID 8831 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].[CH3:18][NH:19][CH3:20]>C(Cl)Cl>[CH3:18][N:19]([CH3:20])[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

4

Reactant 2

HCID 674DimethylamineHCID 18738445HCID 18738445, compound

Product 1

HCID 18738447HCID 18738447, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A 100 mL round bottomed flask equipped with magnetic stir bar was charged with 1.7 g benzyl 3-chlorosulfonyl-2(R)-methylpropionate from Example 3 in 25 mL CH2Cl2. The solution was cooled to −78° C. and 15 mL of anhydrous dimethylamine was slowly added. After 30 minutes the reaction was concentrated in vacuo and the residue was partioned between EA/H2O. The organic phase was dried, concentrated in vacuo to yield 1.4 g of benzyl 3-[(dimethylamino)sulfonyl]-2(R)-methylpropionate as a clear amber oil which was used directly in the next step.

Workup

  1. customA 100 mL round bottomed flask equipped with magnetic stir bar
  2. concentrationAfter 30 minutes the reaction was concentrated in vacuo
  3. customThe organic phase was dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32b557efdea34c5b8be247dea7329d6c
Source dataset
uspto-grants-2006_08
Patent number
US07091219B2

Reaction notes

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