Dicyclohexylcarbodiimide → HCID 67874079, compound

HRID 1418688Notes

Reaction equation

HRID 1418688 reaction equation
[CH3:1][C:2]([CH3:12])([O:4][C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6])[CH3:3].C1(N=C=NC2CCCCC2)CCCCC1.O[CH:29]([C:32]1[CH:48]=[C:47]2[N:35]([CH2:36][C:37]3[C:38]2=[N:39][C:40]2[C:45]([CH:46]=3)=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34](=[O:49])[C:33]=1[CH3:50])[CH2:30][CH3:31]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:50][C:33]1[C:34](=[O:49])[N:35]2[C:47](=[CH:48][C:32]=1[CH:29]([O:10][C:9](=[O:11])[CH2:8][NH:7][C:5]([O:4][C:2]([CH3:12])([CH3:1])[CH3:3])=[O:6])[CH2:30][CH3:31])[C:38]1=[N:39][C:40]3[C:45]([CH:46]=[C:37]1[CH2:36]2)=[CH:44][CH:43]=[CH:42][CH:41]=3

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 613105HCID 613105, compound

Product 1

HCID 67874079HCID 67874079, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-[(1,1-dimethylethoxy)carbonyl]glycine (1.15 g, 6.6 mmol) in CH2Cl2 (50 mL) under an argon atmosphere was added 1,3-dicyclohexylcarbodiimide (1.35 g, 6.5 mmol). After stirring at room temperature for 0.5 h, (±)-7-(1-hydroxypropyl)-8-methylindolizino[1,2-b]quinolin-9(11H)-one (1.0 g, 3.3 mmol) was added followed by a few mg of 4-dimethylaminopyridine. The resulting mixture was allowed to stir at room temperature overnight and then was filtered. The filtrate was washed successively with 2.5% aqueous NaHCO3 (100 mL), 0.1N HCl (100 mL) and H2O (100 mL), dried over sodium sulfate and concentrated in vacuo. The solid residue was purified by column chromatography on silica gel eluting with a solvent gradient of 0-2% MeOH/CH2Cl2 to provide the title compound. 1H NMR (CDCl3) d 8.34 (s, 1H), 8.21 (d, J=8.8 Hz, 1H), 7.91, (d, J=8.3 Hz, 1H), 7.81, (m, 1H), 7.63, (m 1H), 7.32 (s, 1H), 5.96 (apparent br t, J=7.0 Hz, 1H), 5.25 (s, 2H), 5.03 (br s, 1H), 4.15-3.94 (m, 2H), 2.36 (s, 3H), 2.04-184 (m, 2H), 1.44 (s, 9H), 0.99 (t, J=7.4 Hz, 3H). Anal. Calcd for C26H29N3O5.1/8 H2O: C, 67.04; H, 6.33; N, 9.02. Found: C, 66.95; H, 6.54; N, 8.83.

Workup

  1. stirringto stir at room temperature overnight
  2. filtrationwas filtered
  3. washThe filtrate was washed successively with 2.5% aqueous NaHCO3 (100 mL), 0.1N HCl (100 mL) and H2O (100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe solid residue was purified by column chromatography on silica gel eluting with a solvent gradient of 0-2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-76f94c5f0c4c4e789c0128afc75d4b99
Source dataset
uspto-grants-1999_03
Patent number
US05883255

Reaction notes

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