Dicyclohexylcarbodiimide → HCID 67874023, compound

HRID 1418692Notes

Reaction equation

HRID 1418692 reaction equation
[CH3:1][C:2]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:6])[C:3]([OH:5])=[O:4].C1(N=C=NC2CCCCC2)CCCCC1.O[CH:31]([C:34]1[CH:50]=[C:49]2[N:37]([CH2:38][C:39]3[C:40]2=[N:41][C:42]2[C:47]([CH:48]=3)=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36](=[O:51])[C:35]=1[CH3:52])[CH2:32][CH3:33]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:52][C:35]1[C:36](=[O:51])[N:37]2[C:49](=[CH:50][C:34]=1[CH:31]([O:4][C:3](=[O:5])[C:2]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:1])[CH3:6])[CH2:32][CH3:33])[C:40]1=[N:41][C:42]3[C:47]([CH:48]=[C:39]1[CH2:38]2)=[CH:46][CH:45]=[CH:44][CH:43]=3

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 613105HCID 613105, compoundHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

Product 1

HCID 67874023HCID 67874023, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture containing 2-methyl-2-[N-[(1,1-dimethylethoxy)carbonyl]amino]propionic acid (406 mg, 2.0 mmol) and dicyclohexylcarbodiimide (432 mg, 2.0 mmol) in CH2Cl2 (3 mL) under an argon atmosphere were added (±)-7-(1-hydroxypropyl)-8-methylindolizino[1,2-b]quinolin-9(11H)-one (153 mg, 0.5 mmol) and 4-dimethylaminopyridine (25 mg). The resulting mixture was allowed to stir at room temperature for 4 d and then was poured into CH2Cl2, washed successively with 5% aqueous NaHCO3, 0.5N HCl and H2O, and dried over sodium sulfate. Removal of the solvent in vacuo and purification of the residue by column chromatography (silica gel) eluting with a solvent gradient of 1.5-5% MeOH/CH2Cl2 afforded the title compound as an off-white solid. 1H NMR (CDCl3) d 8.33 (s, 1H), 8.20 (d, J=8.9 Hz, 1H), 7.90 (d, J=8.3 Hz, 1H), 7.80 (m, 1H), 7.62 (m, 1H), 7.33 (s, 1H), 5.92 (dd, J=7.5, 6.3 Hz, 1H), 5.25 (s, 2H), 5.10 (br s, 1H), 2.38 (s, 3H), 2.08-1.82 (m, 2H), 1.56 (s, 3H), 1.55 (s, 3H), 1.41 (s, 9H), 0.99 (t, J=7.4 Hz, 3H).

Workup

  1. washwashed successively with 5% aqueous NaHCO3, 0.5N HCl and H2O
  2. dry with materialdried over sodium sulfate
  3. customRemoval of the solvent
  4. customin vacuo and purification of the residue by column chromatography (silica gel)
  5. washeluting with a solvent gradient of 1.5-5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-fb84cae122dc46eda2d56ca6b666ec51
Source dataset
uspto-grants-1999_03
Patent number
US05883255

Reaction notes

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