Benzyloxycarbonylglycine → HCID 21192210, compound

HRID 1067181Notes

Reaction equation

HRID 1067181 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][C:31]([OH:33])=O)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OC1C=[CH:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)N1C(OCC)=O)C>O1CCCC1.C1(C)C=CC=CC=1>[CH2:19]([O:26][C:27]([NH:29][CH2:30][C:31]([N:1]1[CH2:18][CH2:17][N:16]([C:31](=[O:33])[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:31](=[O:33])[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:31](=[O:33])[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:31](=[O:33])[CH2:30][NH:29][C:27]([O:28][CH2:45][C:44]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[O:26])[CH2:6][CH2:5][N:4]([C:31](=[O:33])[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:33])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 14349BenzyloxycarbonylglycineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 41779Hexaaza-18-crown-6

Product 1

HCID 21192210HCID 21192210, 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 3.14 g (15 mmol) of benzyloxycarbonyl-glycine (Fluka) 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 completion of the reaction, the product is precipitated by adding hexane, and the precipitate is chromatographed with dichloromethane/hexane/isopropanol (20:10:1) on silica gel.

Workup

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

Sources & evidence

ORD record
ord-df03dfb64d2742a0b847682ad9e10cf2
Source dataset
uspto-grants-2001_06
Patent number
US06248306B1

Reaction notes

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