3,4-Dichloro-2-hydroxybenzoic acid → Phenylalanine ethyl ester

HRID 1969306Notes

Reaction equation

HRID 1969306 reaction equation
[OH:1][C:2]1[C:21]([Cl:22])=[CH:20][C:19]([Cl:23])=[CH:18][C:3]=1[C:4]([NH:6][C@H:7]([C:15]([OH:17])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5].Cl[C:25]1C(Cl)=C(O)[C:28](=C[CH:33]=1)[C:29](O)=[O:30].C(OCC(OC1C(Cl)=CC(Cl)=CC=1C(O)=O)=O)(=O)C.[C:55]([O:58][CH2:59][C:60]([O:62][C:63]1[C:71]([Cl:72])=[CH:70][C:69]([Cl:73])=[CH:68][C:64]=1[C:65]([Cl:67])=[O:66])=[O:61])(=[O:57])[CH3:56]>>[C:55]([O:58][CH2:59][C:60]([O:62][C:63]1[C:71]([Cl:72])=[CH:70][C:69]([Cl:73])=[CH:68][C:64]=1[C:65]([Cl:67])=[O:66])=[O:61])(=[O:57])[CH3:56].[CH2:25]([O:17][C:15](=[O:16])[C@H:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[NH2:6])[CH3:33].[C:29]([O:1][C:2]1[C:21]([Cl:22])=[CH:20][C:19]([Cl:23])=[CH:18][C:3]=1[C:4]([NH:6][C@H:7]([C:15]([OH:17])=[O:16])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])(=[O:30])[CH3:28]

Participants

7

Reactant 4

HCID 290781033,4-Dichloro-2-hydroxybenzoic acidHCID 51037939N-(2-hydroxy-3,5-dichlorobenzoyl)-L-phenylalanineHCID 669062922-Acetoxyacetoxy-3,5-dichlorobenzoic acid2×HCID 871989572-Acetoxyacetoxy-3,5-dichlorobenzoic acid chloride

Product 3

HCID 76506Phenylalanine ethyl esterHCID 66906696N-(2-acetoxy-3,5-dichlorobenzoyl)-L-phenylalanineHCID 871989572-Acetoxyacetoxy-3,5-dichlorobenzoic acid chloride

Procedure

The invention also provides a method for synthesizing N-(2-hydroxy-3,5-dichlorobenzoyl)-L-phenylalanine, comprising: converting 3-5 dichlorosalicylic acid into 2-acetoxyacetoxy-3,5-dichlorobenzoic acid; converting 2-acetoxyacetoxy-3,5-dichlorobenzoic acid into 2-acetoxyacetoxy-3,5-dichlorobenzoic acid chloride; reacting 2-acetoxyacetoxy-3,5-dichlorobenzoic acid chloride with L-phenylalanine ethyl ester to form N-(2-acetoxy-3,5-dichlorobenzoyl)-L-phenylalanine; and converting N-(2-acetoxy-3,5-dichlorobenzoyl)-L-phenylalanine into N-(2-hydroxy-3,5-dichlorobenzoyl)-L-phenylalanine. In some embodiments, the converting comprises hydrolyzing of ester functions in N-(2-acetoxy-3,5-dichlorobenzoyl)-L-phenylalanine.

Workup

  1. customThe invention also provides a method

Sources & evidence

ORD record
ord-a20319d3aedd48f2a3958b86194ec178
Source dataset
uspto-grants-2013_04
Patent number
US08426541B2

Reaction notes

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