Ethyl chloroformate → Ethyl 1-[1-(aminocarbonyl)cyclobutyl]-6-chloro-1,3,4,9-tetrahydro-2H-beta-carboline-2-carboxylate

HRID 1700375Notes

Reaction equation

HRID 1700375 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[OH-].[NH4+:8].[Cl:9][C:10]1[CH:11]=[C:12]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]1[CH:17]([C:23]3([C:27]([OH:29])=O)[CH2:26][CH2:25][CH2:24]3)[NH:16][CH2:15][CH2:14][C:13]2=1>O1CCCC1.CN1CCOCC1>[NH2:8][C:27]([C:23]1([CH:17]2[C:18]3[NH:19][C:20]4[C:12](=[CH:11][C:10]([Cl:9])=[CH:22][CH:21]=4)[C:13]=3[CH2:14][CH2:15][N:16]2[C:2]([O:4][CH2:5][CH3:6])=[O:3])[CH2:26][CH2:25][CH2:24]1)=[O:29]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 183178661-(6-Chloro-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxylic Acid

Product 1

HCID 18317856Ethyl 1-[1-(aminocarbonyl)cyclobutyl]-6-chloro-1,3,4,9-tetrahydro-2H-beta-carboline-2-carboxylate

Reagents, catalysts & solvents 2

HCID 79724-MethylmorpholineSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.3 ml of ethyl chloroformate, and then 0.2 ml of a 28% ammonium hydroxide solution, are added at −10° C. to a solution of 1 g of the compound of Example 32 in 50 ml of tetrahydrofuran and 0.5 ml of N-methylmorpholine. After reaction for 12 hours, the solvent is distilled off; the residue is then taken up in a water/dichloromethane mixture. The expected product is isolated by decanting, drying and concentrating under reduced pressure.

Workup

  1. customAfter reaction for 12 hours
  2. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-f6fe23909693411f933ee01e38a78290
Source dataset
uspto-grants-2002_02
Patent number
US06350757B1

Reaction notes

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