1,2-Dichloroethane → HCID 60596107, compound

HRID 2184938Notes

Reaction equation

HRID 2184938 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:15][CH3:16])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[C:17]([O:21][C:22]([NH:24][CH2:25][C:26](O)=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18].C(Cl)CCl>C(Cl)Cl.C(OCC)(=O)C>[C:17]([O:21][C:22](=[O:23])[NH:24][CH2:25][C:26](=[O:27])[NH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:15][CH3:16])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3)([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 85883-Amino-9-ethylcarbazoleHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 60596107HCID 60596107, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-9-ethylcarbazole (8.1 g, 38 mmol), tert-butoxycarbonylamino-acetic acid (6.7 g, 38 mmol), and N,N-dimethylaminopyridine (5.7 g, 46 mmol) in CH2Cl2 (125 mL) was added EDC (5.5 g, 46 mmol). The resultant solution was stirred at room temperature for 2 days, and then diluted with ethyl acetate (500 mL) and washed with aqueous 1 M HCl (2×100 mL), water (100 mL), saturated aqueous NaHCO3 (100 mL), and then brine (100 mL). The organic layer was then dried (Na2SO4), concentrated under reduced pressure, and then flash chromatographed (silica, 1:39 to 1:19 to 1:9 ethyl acetate/CH2Cl2) to afford [(9-ethyl-9H-carbazol-3-ylcarbamoyl)-methyl]-carbamic acid tert-butyl ester (9.1 g, 65%) as a brown foam. MS m/z @ 368 (M+1).

Workup

  1. washwashed with aqueous 1 M HCl (2×100 mL), water (100 mL), saturated aqueous NaHCO3 (100 mL)
  2. dry with materialThe organic layer was then dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customflash chromatographed (silica, 1:39 to 1:19 to 1:9 ethyl acetate/CH2Cl2)

Sources & evidence

ORD record
ord-64043c85b8ff46ca9c2a5d785fdb9224
Source dataset
uspto-grants-2002_06
Patent number
US06399631B1

Reaction notes

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