Water → HCID 86754411, compound

HRID 1585539Notes

Reaction equation

HRID 1585539 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])[O-].[Na+].[Na+].O>CN1C(=O)N(C)CCC1.C(OCC)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[CH2:10][NH:11][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 53666280HCID 53666280, compound

Product 1

HCID 86754411HCID 86754411, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

To a solution of (1R)-N1 -(tert-butoxycarbonyl)-1-(1H-indol-3-ylmethyl)-1,2-ethanediamine (1.00 g) in N,N'-dimethylpropyleneurea (10 ml) were added successively ethyl 4-bromobutyrate (0.49 ml) and sodium carbonate (0.73 g) at room temperature in a stream of nitrogen. The mixture was stirred at the same temperature for 45 minutes and then at 110° C. for 3 hours. After cooling to room temperature, water (100 ml) and diethyl ether (50 ml) were added into the mixture. The organic layer was separated and washed with brine, and dried over magnesium sulfate. After evaporation in vacuo, the residue was purified by column chromatography on silica gel (35 g) eluting with a mixture of dichloromethane-methanol (from 0% to 6% gradient solution) to give (1R)-N1 -(tert-butoxycarbonyl)-N2 -[3-(ethoxycarbonyl)-propyl]-1-(1H-indol-3-ylmethyl)-1,2-ethanediamine (0.78 g) as an oil.

Workup

  1. waitat 110° C. for 3 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation in vacuo
  6. customthe residue was purified by column chromatography on silica gel (35 g)
  7. washeluting with a mixture of dichloromethane-methanol (from 0% to 6% gradient solution)

Sources & evidence

ORD record
ord-e30a88001d564e9b9e8e7efef1673994
Source dataset
uspto-grants-1999_08
Patent number
US05939413

Reaction notes

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