Methyl L-phenylalaninate hydrochloride → HCID 53816216, compound

HRID 2229815Notes

Reaction equation

HRID 2229815 reaction equation
[Cl:1][C:2]1[C:3]([OH:13])=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[OH:11])[C:5]([OH:7])=O.Cl.[CH3:15][O:16][C:17](=[O:27])[C@H:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH2:19].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(N(CC)CC)C>[CH3:15][O:16][C:17](=[O:27])[C@H:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:19][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([Cl:12])[C:10]([OH:11])=[C:2]([Cl:1])[C:3]=1[OH:13]

Participants

7

Reactant 4

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3042133beta-Resorcylic acid, 3,5-dichloro-

Product 1

HCID 53816216HCID 53816216, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3,5-dichloro-2,4-dihydroxybenzoic acid (17 g), L-phenylalanine methyl ester hydrochloride (19.8 g), WSC.HCl (17.6 g) and HOBT (12.4 g) in DMF (70 ml) was added dropwise triethylamine (12.8 ml) at room temperature, and the mixture was stirred for 16 hours. Then, the mixture was post-treated in the same manner as in the above Example 1, Step 5) to give the title compound (18.32 g, yield 57%).

Workup

  1. additionThen, the mixture was post-treated in the same manner as in the above Example 1, Step 5)

Sources & evidence

ORD record
ord-80de33137abe486b93570a4ef239340a
Source dataset
uspto-grants-2002_07
Patent number
US06420561B1

Reaction notes

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