Hydrochloric Acid → HCID 53896521, compound

HRID 1585541Notes

Reaction equation

HRID 1585541 reaction equation
C(OC([NH:8][C@H:9]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[CH2:10][NH:11][C:12](=[O:15])[CH2:13][Br:14])=O)(C)(C)C.Cl>C(OCC)(=O)C>[Br:14][CH2:13][C:12]([NH:11][CH2:10][C@@H:9]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[NH2:8])=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53656844HCID 53656844, compound

Product 1

HCID 53896521HCID 53896521, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To an ice-cooled solution of (1R)-N1 -(tert-butoxycarbonyl)-N2 -(bromoacetyl)-1-(1H-indol-3-ylmethyl)-1,2-ethanediamine (9.32 g) in ethyl acetate (90 ml) was added 4N hydrogen chloride in ethyl acetate solution (90 ml). The mixture was stirred at the same temperature for 50 minutes and then evaporated under reduced pressure. Dichloromethane and aqueous saturated sodium bicarbonate solution were added to the residue. The organic layer was separated. The aqueous layer was extracted six times with dichloromethane. The extracts were combined and dried over magnesium sulfate, and concentrated under reduced pressure to give (1R)-N2 -(bromoacetyl)-1-(1H-indol-3-ylmethyl)-1,2-ethanediamine (3.01 g) as an oil.

Workup

  1. customevaporated under reduced pressure
  2. additionDichloromethane and aqueous saturated sodium bicarbonate solution were added to the residue
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted six times with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-28d6536c39ab4d4b9da89a089bfd4ee2
Source dataset
uspto-grants-1999_08
Patent number
US05939413

Reaction notes

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