Triethylamine → HCID 11580173, compound

HRID 1669358Notes

Reaction equation

HRID 1669358 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:19])[C@H:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[NH2:13].[CH:20]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26])=[O:21]>O1CCCC1>[CH3:9][O:10][C:11](=[O:19])[CH:12]([NH:13][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][CH:30]=[C:22]([CH:20]=[O:21])[CH:23]=1)[CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734892L-Aspartic acid, 1,4-dimethyl ester, hydrochloride (1:1)HCID 152388213-Formylbenzoyl chloride

Product 1

HCID 11580173HCID 11580173, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 30 ml of tetrahydrofuran, 12 ml of triethylamine and 4.11 g of aspartic acid dimethyl ester hydrochloride was added dropwise to a solution of 3.50 g of 3-formylbenzoic acid chloride in 30 ml of tetrahydrofuran at 10° C. After stirred at room temperature for 6 hours, insolubles were filtered and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 3.01 g of oily 2-[3-formyl-(benzoylamino)]succinic acid dimethyl ester [Compound No. (p)].

Workup

  1. filtrationinsolubles were filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-541a3e0b4f7846c0b6350026313445f4
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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