110994-91-7 → HCID 53823235, compound

HRID 849373Notes

Reaction equation

HRID 849373 reaction equation
[Br:1][C@H:2]([CH2:6][OH:7])[C:3]([OH:5])=[O:4].[C:8](OC(=N)N(C(C)C)C(C)C)([CH3:11])([CH3:10])[CH3:9]>C(Cl)(Cl)Cl>[Br:1][C@H:2]([CH2:6][OH:7])[C:3]([O:5][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:4]

Participants

4

Reactant 2

HCID 13776211110994-91-7HCID 22010542tert-Butyl N,N-dipropan-2-ylcarbamimidate

Product 1

HCID 53823235HCID 53823235, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

18.1 g of (2R)-2-bromo-3-hydroxypropionic acid and 200 ml of chloroform were mixed, and 53.6 g of O-tert-butyl-N,N-diisopropylisourea was added under cooling with ice, followed by stirring at room temperature for 15 hours. Insoluble matters were filtered off, and then, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1) to obtain 14.7 g (yield: 61%) of the above identified compound as a colorless oily substance.

Workup

  1. temperatureunder cooling with ice
  2. filtrationInsoluble matters were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1)
  5. customto obtain 14.7 g (yield: 61%) of the

Sources & evidence

ORD record
ord-93f00563833a486caa1041b9386f716b
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

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