Triethylamine → HCID 90281983, compound

HRID 1497546Notes

Reaction equation

HRID 1497546 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].Cl.[NH2:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(N(CC)CC)C>C(#N)C>[C:13]([O:12][C:10](=[O:11])[CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][NH:18][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 117787558HCID 117787558, compound

Product 1

HCID 90281983HCID 90281983, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl [2-(chloromethyl)phenyl]acetate (2.31 g) in acetonitrile (23.1 mL) were added tert-butyl glycinate hydrochloride (2.41 g) and triethylamine (4.01 mL), followed by heating at 60° C. for 3 hours. The reaction suspension was concentrated under reduced pressure, then to the residue were added water and ethyl acetate, and the organic layer was extracted. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl N-[2-(2-tert-butoxy-2-oxoethyl)benzyl]glycinate (2.54 g).

Workup

  1. concentrationThe reaction suspension was concentrated under reduced pressure
  2. additionto the residue were added water and ethyl acetate
  3. extractionthe organic layer was extracted
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-cd91c40870c7472faade22b7f028fffc
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

Loading…