Methyl L-phenylalaninate hydrochloride → HCID 86756228, compound

HRID 566414Notes

Reaction equation

HRID 566414 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=N[CH2:33][CH2:34][CH2:35][N:36]([CH3:38])C.Cl.[CH:40]1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(N(CC)CC)C>[ClH:1].[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]([O:11][CH2:40][CH2:33][CH2:34][CH2:35][NH:36][CH3:38])=[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 86756228HCID 86756228, compoundYield 95%

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-085fae59107b4fb8a96c6fe0afb59b3b
Source dataset
uspto-grants-2001_01
Patent number
US06174887B1

Reaction notes

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