Eugenol → Amino-acetic acid 4-allyl-2-methoxy-phenyl ester

HRID 82490

Reaction equation

HRID 82490 reaction equation
[C:1]1([O:11][CH3:12])[C:2](=[CH:4][CH:5]=[C:6]([CH:10]=1)[CH2:7][CH:8]=[CH2:9])[OH:3].C([NH:20][CH2:21][C:22](O)=[O:23])(OC(C)(C)C)=O.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:7]([C:6]1[CH:5]=[CH:4][C:2]([O:3][C:22](=[O:23])[CH2:21][NH2:20])=[C:1]([O:11][CH3:12])[CH:10]=1)[CH:8]=[CH2:9]

Participants

7

Reactant 4

HCID 3314EugenolHCID 79724-MethylmorpholineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 69920127Amino-acetic acid 4-allyl-2-methoxy-phenyl esterYield 74.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of Eugenol (0.3 g, 1.82 mmol) in DCM (20 mL), was added Boc-glycine (0.35 g, 2.01 mmol), N-methyl morpholine (0.65 mL, 6.00 mmol), EDC.HCl (0.76 g, 4.0 mmol) and DMAP at ice temperature. The mixture was allowed to stir at room temperature (25° C.) over a period of 12 h. The resulting mixture was diluted with DCM (100 mL), washed with water (2×50 mL) and dried over sodium sulphate. The crude product obtained upon evaporation of the solvent was purified by silica gel column chromatography to obtain resulting product as pale yellow oil (300 mg, 46.9%)

Workup

  1. washwashed with water (2×50 mL)
  2. dry with materialdried over sodium sulphate
  3. customThe crude product obtained upon evaporation of the solvent
  4. customwas purified by silica gel column chromatography
  5. customto obtain

Sources & evidence

ORD record
ord-20563f5d9d02499d865f4a5bbbe742c0
Source dataset
uspto-grants-2014_09
Patent number
US08846721B2

Linked notes

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