N-Cbz-d-alanine → HCID 22867053, compound

HRID 1900762Notes

Reaction equation

HRID 1900762 reaction equation
[NH2:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.[C:18]([NH:28][C@@H:29]([C:31](O)=[O:32])[CH3:30])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[C:18]([NH:28][C@@H:29]([C:31]([NH:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3)=[O:32])[CH3:30])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]

Participants

6

Reactant 4

HCID 70832N-Cbz-d-alanineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 233695672-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

Product 1

HCID 22867053HCID 22867053, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (2.3 g, 10 mmol) was dissolved in dimethylformamide (100 ml) while cooled on ice. To the obtained mixture, carbobenzyloxy-D-alanine (2.3 g, 10.5 mmol), WSC.HCl (2.3 g, 11.0 mmol), and HOBT (1.4 g, 11.0 mmol) were added, and the resultant mixture was stirred at room temperature for two days. The reaction mixture was condensed under reduced pressure. The obtained residue was extracted with chloroform, washed with 1N-HCl, saturated aqueous NaCl solution, and dried over magnesium sulfate anhydride. The solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform: methanol=15:1) to obtain 4.27 g of the title compound as colorless powdery crystals (98.0%)

Workup

  1. temperaturewhile cooled on ice
  2. customcondensed under reduced pressure
  3. extractionThe obtained residue was extracted with chloroform
  4. washwashed with 1N-HCl, saturated aqueous NaCl solution
  5. dry with materialdried over magnesium sulfate anhydride
  6. customThe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (chloroform: methanol=15:1)

Sources & evidence

ORD record
ord-3674e8cb00254320908e98f236729fb1
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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