Dicyclohexylcarbodiimide → HCID 178422604, compound

HRID 345206Notes

Reaction equation

HRID 345206 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1([CH3:18])[O:9][C:8]2[C:10]([CH3:17])=[C:11]([CH3:16])[C:12]([OH:15])=[C:13]([CH3:14])[C:7]=2[CH2:6][CH2:5]1.[ClH:19].[NH:20]([C:24]1[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=1)[C:21]([NH2:23])=[NH:22].C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1.CN(C)C=O>[ClH:19].[OH:15][C:12]1[C:11]([CH3:16])=[C:10]([CH3:17])[C:8]2[O:9][C:4]([CH2:3][CH2:2][NH:1][C:28](=[O:29])[C:27]3[CH:26]=[CH:25][C:24]([NH:20][C:21]([NH2:23])=[NH:22])=[CH:32][CH:31]=3)([CH3:18])[CH2:5][CH2:6][C:7]=2[C:13]=1[CH3:14]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 200967022-(2-aminoethyl)-2,5,7,8-tetramethyl-6-hydroxy-3,4-dihydro-2H-benzo[1,2-b]pyranHCID 178479383HCID 178479383, compound

Product 1

HCID 178422604HCID 178422604, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

The amine (prepared in reference example 3, 1.0 g) and 4-guanidinobenzoic acid hydrochloride (0.95 g) were dissolved in the mixture of pyridine (5 ml) and dimethylformamide (5 ml). Dicyclohexylcarbodiimide (0.91 g) was added to the solution. The mixture was stirred for 2.5 days. The reaction solution was filtered. The filtrate was evaporated. The residue was dissolved in methanol (10 ml), and 1N hydrochloric acid (6 ml) was added to the solution. The solution was evaporated. The residue was purified by column chromatography on silica gel (methylene chloride: methanol=10:1) to give the title compound (275 mg) having the following physical data.

Workup

  1. filtrationThe reaction solution was filtered
  2. customThe filtrate was evaporated
  3. dissolutionThe residue was dissolved in methanol (10 ml)
  4. addition1N hydrochloric acid (6 ml) was added to the solution
  5. customThe solution was evaporated
  6. customThe residue was purified by column chromatography on silica gel (methylene chloride: methanol=10:1)

Sources & evidence

ORD record
ord-c3e06254f48b4ddc8817aafbe6fc5e66
Source dataset
uspto-grants-1991_10
Patent number
US05055598

Reaction notes

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