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N-Benzyloxycarbonyl-beta-alanine → 2-(Carbobenzyloxy-beta-alanyl]aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900771
Notes
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Reaction equation

HRID 1900771 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][CH2:29][CH2:30][C:31](O)=[O:32])([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][CH2:29][CH2:30][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])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 75313N-Benzyloxycarbonyl-beta-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 678009322-(Carbobenzyloxy-beta-alanyl]aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one
Yield 46.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (3.00 g, 13.0 mmol) was dissolved in dimethylformamide (200 ml). To this solution, N-carbobenzyloxy-β-alanine (4.40 g, 19.5 mmol), WSC-HCl (3.50 g, 19.5 mmol), and HOBT (1.00 g, 7.2 mmol) were added, and the mixture was stirred at room temperature for 48 hours. The reaction mixture was condensed under reduced pressure, and the residue was subjected to extraction using a solvent mixture (chloroform--methanol =4:1) combined with 1N-HCl. The organic phase was washed with saturated aqueous NaCl solution, followed by drying and condensing under reduced pressure. The resultant residue was recrystallized from chloroform--methanol--ether. As a result, 2.61 g of the title compound was obtained as colorless powdery crystals (46.2%).

Workup

  1. customcondensed under reduced pressure
  2. extractionthe residue was subjected to extraction
  3. washThe organic phase was washed with saturated aqueous NaCl solution
  4. customby drying
  5. customcondensing under reduced pressure
  6. customThe resultant residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-04d22481f2544d17a5171fd1079370bb
Source dataset
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05576324

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes