Methyl L-phenylalaninate hydrochloride → HCID 53816216, compound

HRID 1822605Notes

Reaction equation

HRID 1822605 reaction equation
[Cl:1][CH:2]1[C:10](Cl)([OH:11])[CH:9]=[CH:8][C:4]([C:5]([OH:7])=O)=[C:3]1[OH:13].[ClH:14].[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:14])[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 69621019HCID 69621019, compound

Product 1

HCID 53816216HCID 53816216, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3,4-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-a7e1308cf54448cca57929d0b63ed123
Source dataset
uspto-grants-2006_05
Patent number
USRE039088E1

Reaction notes

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