HCID 86583573, compound → HCID 86583571, compound

HRID 1790593Notes

Reaction equation

HRID 1790593 reaction equation
Cl.C([O:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:7]=1[CH:14]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[NH:29])[NH2:28])=[CH:23][CH:22]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])C=C.[H][H]>C(O)C.[Pt](=O)=O>[ClH:12].[C:27]([C:24]1[CH:25]=[CH:26][C:21]([NH:20][CH:14]([C:7]2[CH:8]=[C:9]([Cl:13])[CH:10]=[C:11]([Cl:12])[C:6]=2[OH:5])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:22][CH:23]=1)(=[NH:28])[NH2:29]

Participants

5

Reactant 2

HCID 86583573HCID 86583573, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86583571HCID 86583571, compoundYield 197.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 300 mg of ethyl (RS)-(2-allyloxy-3,5-dichloro-phenyl)-(4-carbamimidoyl-phenylamino)-acetate hydrochloride (1:1) (see Example 293.3) in 5 ml of ethanol was treated with hydrogen in ther presence of a catalytic amount of platinum dioxide for 45 minutes while stirring. The reaction mixture was suction filtered over Speedex. The filtrate was concentrated and gave 270 mg of ethyl (RS)-(4-carbamimidoyl-phenylamino)-(3,5-dichloro-2-hydroxy-phenyl)-acetate hydrochloride (1:1); MS (ISP) m/z 382/384 (M+H)+.

Workup

  1. filtrationfiltered over Speedex
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-15d64ebc0267416093291a352eeb1610
Source dataset
uspto-grants-2006_07
Patent number
US07071212B2

Reaction notes

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