Dichloromethane → HCID 53656844, compound

HRID 1585540Notes

Reaction equation

HRID 1585540 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].ClCCl.C(=O)([O-])[O-].[K+].[K+].[Br:31][CH2:32][C:33](Cl)=[O:34]>O.CN(C)C=O>[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][C:33](=[O:34])[CH2:32][Br:31])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium Carbonate2×HCID 89602Bromoacetyl chloride2×HCID 53666280HCID 53666280, compound

Product 1

HCID 53656844HCID 53656844, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of (1R)-N1 -(tert-butoxycarbonyl)-1-(1H-indol-3-ylmethyl)-1,2-ethanediamine (7.00 g) in a mixed solvent of dichloromethane (200 ml) and dimethylformamide (200 ml) was added potassium carbonate (10.03 g). To the mixture was added dropwise bromoacetyl chloride (7.61 g) for 3 minutes, and then the mixture was stirred at the same temperature for 1 hour and 40 minutes by adding further potassium carbonate (3.34 g) and bromoacetyl chloride (2.00 ml) into the mixture. The resulting mixture was poured into water, and extracted twice with dichloromethane. The extracts were combined and washed successively with 0.5N hydrochloric acid and brine, and dried over magnesium sulfate. After evaporation in vacuo, the residue was dried to give (1R)-N1 -(tert-butoxycarbonyl)-N2 -(bromoacetyl)-1-(1H-indol-3-ylmethyl)-1,2-ethanediamine (9.9 g) as crystal.

Workup

  1. extractionextracted twice with dichloromethane
  2. washwashed successively with 0.5N hydrochloric acid and brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporation in vacuo
  5. customthe residue was dried

Sources & evidence

ORD record
ord-e1436d54f2724f29ada52f8686dfd725
Source dataset
uspto-grants-1999_08
Patent number
US05939413

Reaction notes

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