Water → HCID 118113219, compound

HRID 1485123Notes

Reaction equation

HRID 1485123 reaction equation
[C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:6])[CH2:2][C:3]([O-:5])=O.[C:15](Cl)([CH3:18])([CH3:17])[CH3:16].[NH2:20][CH2:21][C:22]([OH:24])=[O:23].C(N(CC)CC)C.O>CN(C)C=O>[CH3:16][C:15]([O:24][C:22](=[O:23])[CH2:21][NH:20][C:3](=[O:5])[CH2:2][C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 22247814Benzyl malonateHCID 86595916HCID 86595916, compound

Product 1

HCID 118113219HCID 118113219, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of monobenzyl malonate (2.00 g) in N,N-dimethylformamide (51.5 mL), glycine tert-butyl hydrochloride (2.07 g), triethylamine (3.13 g) and propylphosphonic acid anhydride (cyclic trimer) (48%, solution in N,N-dimethylformamide, 8.22 g) were added and the mixture was stirred at room temperature for an hour. To the reaction mixture, water was added and extraction was conducted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=67:33-50:50) to give benzyl 3-({2-[(2-methyl-2-propanyl)oxy]-2-oxoethyl}amino)-3-oxopropanoate as a colorless oil (1.46 g).

Workup

  1. extractionextraction
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. customThe desiccant was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=67:33-50:50)

Sources & evidence

ORD record
ord-ad96a83057714dd9bad4d0d957d5c4f7
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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