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

HRID 363272Notes

Reaction equation

HRID 363272 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-l-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-83125fe5b11f4415b042080e20951a94
Source dataset
uspto-grants-1999_02
Patent number
US05874061

Reaction notes

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