2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 18790420, compound

HRID 1106969Notes

Reaction equation

HRID 1106969 reaction equation
[NH:1]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:19]([O:26][C:27]([NH:29][CH2:30][CH2:31][C:32]([OH:34])=O)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OC1C=[CH:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)N1C(OCC)=O)C>O1CCCC1.C1(C)C=CC=CC=1>[CH2:19]([O:26][C:27]([NH:29][CH2:30][CH2:31][C:32]([N:1]1[CH2:18][CH2:17][N:16]([C:32](=[O:34])[CH2:31][CH2:30][NH:29][C:27]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:28])[CH2:15][CH2:14][N:13]([C:32](=[O:34])[CH2:31][CH2:30][NH:29][C:27]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:28])[CH2:12][CH2:11][N:10]([C:32](=[O:34])[CH2:31][CH2:30][NH:29][C:27]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:28])[CH2:9][CH2:8][N:7]([C:32](=[O:34])[CH2:31][CH2:30][NH:29][C:27]([O:28][CH2:46][C:45]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:26])[CH2:6][CH2:5][N:4]([C:32](=[O:34])[CH2:31][CH2:30][NH:29][C:27]([O:26][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:28])[CH2:3][CH2:2]1)=[O:34])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 41779Hexaaza-18-crown-6HCID 75313N-Benzyloxycarbonyl-beta-alanine

Product 1

HCID 18790420HCID 18790420, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

516 mg (2 mmol) of 1,4,7,10,13,16-hexaazacyclooctadecane (hexacyclene; Fluka) is azeotropically dehydrated with toluene. A solution of 3.35 g (15 mmol) of benzyloxycarbonyl-β-alanine (Sigma) in tetrahydrofuran (THF) as well as 3.71 g (15 mmol) of 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ; Fluka) are added to the cooled solution of hexacyclene in toluene at room temperature and stirred overnight. After the reaction is completed, the product is precipitated by adding hexane, and the precipitate is chromatographed on silica gel with dichloromethane/hexane/isopropanol (20:10:1).

Workup

  1. customthe product is precipitated
  2. additionby adding hexane
  3. customthe precipitate is chromatographed on silica gel with dichloromethane/hexane/isopropanol (20:10:1)

Sources & evidence

ORD record
ord-4071472a056e4f2693dc43a5ae81ec8e
Source dataset
uspto-grants-2000_05
Patent number
US06057419

Reaction notes

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