Methyl Acrylate → HCID 68291126, compound

HRID 1487313Notes

Reaction equation

HRID 1487313 reaction equation
CO[C:3](=[O:16])[CH2:4][NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19].[H-].[Na+]>C1(C)C=CC=CC=1>[O:16]=[C:3]1[CH2:4][N:5]([C:6]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7])[CH2:19][CH:18]1[C:17]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 24758Sodium hydrideHCID 71033Methyl N-benzyloxycarbonylglycinate

Product 1

HCID 68291126HCID 68291126, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of carbobenzyloxyglycine methyl ester (10 g, 44.8 mmol) and methyl acrylate (4.03 mL, 44.8 mmol) in toluene (100 mL) at 0° C. was added 60% NaH in mineral oil (1.971 g, 49.3 mmol) which was stirred for 10 minutes, and then it was warmed up to RT and stirred for 20 minutes. The reaction mixture was heated to 50° C. for 3 hrs. The reaction mixture was quenched with 10% citric acid solution until pH about 3, and then it was extracted with 100 mL×3 of EtOAc. The combined organic phases were washed with 100 mL of brine and dried over Na2SO4. Filtration and concentration to yield the product (12 g, 96% yield). MS(ES+) m/z: 278.2 (M+H); HPLC retention time: 2.44 min (analytical HPLC Method B).

Workup

  1. stirringstirred for 20 minutes
  2. temperatureThe reaction mixture was heated to 50° C. for 3 hrs
  3. customThe reaction mixture was quenched with 10% citric acid solution until pH about 3
  4. extractionit was extracted with 100 mL×3 of EtOAc
  5. washThe combined organic phases were washed with 100 mL of brine
  6. dry with materialdried over Na2SO4
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-4e818dbd0d0c41dcb9209964897f5dee
Source dataset
uspto-grants-2016_08
Patent number
US09428511B2

Reaction notes

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