Triethylamine → L-Phenylalanine

HRID 1393068Notes

Reaction equation

HRID 1393068 reaction equation
ClC1C=CC=C(C)C=1[C:4]([OH:6])=[O:5].[CH2:12](Cl)[CH2:13]Cl.Cl.[CH:17]1[CH:22]=N[C:20]2[N:23](O)N=N[C:19]=2[CH:18]=1.[CH2:27](N(CC)CC)C>ClCCl>[NH2:23][C@H:20]([C:4]([OH:6])=[O:5])[CH2:19][C:18]1[CH:17]=[CH:22][CH:13]=[CH:12][CH:27]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 888702-Chloro-6-methylbenzoic acidHCID 181649HOAtHCID 22619321HCID 22619321, compound

Product 1

HCID 6140L-Phenylalanine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-chloro-6-methyl benzoic acid (1.7 g), EDC/HCl (1.9 g), HOAt (1.4 g), triethylamine (2.2 mL) and dichloromethane (42 mL) were added to the compound obtained in Process 1 (2.1 g) and stirred overnight. After the reaction mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid, saturated sodium bicarbonate water and saturated aqueous solution of sodium chloride, the organic layer was dried over anhydrous sodium sulfate. The solvent was removed to obtain a crude material of the title compound.

Sources & evidence

ORD record
ord-ed6d0d9a0091440a903c5cb70682d532
Source dataset
uspto-grants-2008_03
Patent number
US07345049B2

Reaction notes

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