Triethylamine → HCID 58310979, compound

HRID 1189589Notes

Reaction equation

HRID 1189589 reaction equation
[C:1]1([CH:7]([CH2:11][C:12](=O)[CH3:13])[C:8](=O)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.[NH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>ClC(Cl)C>[CH3:9][C:8]1[N:23]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:12]([CH3:13])=[CH:11][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 12288236HCID 12288236, compound

Product 1

HCID 58310979HCID 58310979, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirring solution of 3-phenylhexane-2,5-dione (0.330 g, 1.735 mmol) in dichloroethane (5 ml) was added triethylamine (0.725 ml, 5.20 mmol), followed by ethyl 2-aminoacetate hydrochloride (0.291 g, 2.082 mmol). The reaction was stirred overnight at room temperature, after which LCMS showed formation of the desired product. The reaction mixture was purified directly on an ISCO automated chromatography system (silica gel) using an EtOAc/hexane gradient. The desired fractions were collected and concentrated in vacuum and the crude mixture was taken directly to the next step without further purification.

Sources & evidence

ORD record
ord-02d97948b3464a5794ca047684e4f83c
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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