Triethylamine → Ethyl 2-(2-iodo-4,5-dimethoxybenzamido)acetate

HRID 2175712Notes

Reaction equation

HRID 2175712 reaction equation
[I:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[NH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)Cl>[I:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([NH:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:6]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27584222-Iodo-4,5-dimethoxybenzoic acid

Product 1

HCID 67087805Ethyl 2-(2-iodo-4,5-dimethoxybenzamido)acetateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-iodo-4,5-dimethoxybenzoic acid (24.6 g, 80 mmol), ethyl 2-aminoacetate hydrochloride (11 g, 88 mmol), EDCl (17 g, 88 mmol) and HOBt (14 g, 88 mmol) in dry DCM (500 mL) was added Et3N (55 mL, 400 mmol) dropwise at rt. The resulting mixture was stirred at room temperature overnight then the reaction was quenched with water, and thoroughly extracted with DCM. The combined organic phases were washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using petroleum ether/ethyl acetate 3:1 (v:v) as eluent to give ethyl 2-(2-iodo-4,5-dimethoxybenzamido)acetate (29 g, 95%).

Workup

  1. customthe reaction was quenched with water
  2. extractionthoroughly extracted with DCM
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-69c2e5e7112d483f807a47575309e914
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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