Sodium hydride → N-(tert-butoxycarbonyl)-N'-[(2-methyl-6-indolyloxy)-acetyl]-1,4-diamino-butane

HRID 973744Notes

Reaction equation

HRID 973744 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([CH3:13])[NH:10]2)=[CH:6][CH:5]=1.[C:14]([O:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:30])[CH2:28]Cl)=[O:20])([CH3:17])([CH3:16])[CH3:15]>CN(C)C=O>[C:14]([O:18][C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:30])[CH2:28][O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([CH3:13])[NH:10]2)=[CH:6][CH:5]=1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 14751510tert-butyl N-[4-(2-chloroacetamido)butyl]carbamateHCID 148785962-Methyl-1H-indol-6-ol

Product 1

HCID 14878738N-(tert-butoxycarbonyl)-N'-[(2-methyl-6-indolyloxy)-acetyl]-1,4-diamino-butaneYield 156.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.07 g of sodium hydride in suspension in 50% of oil were added progressively to a solution of 3.28 g of 6-hydroxy-2-methyl indole in 50 ml of dimethylformamide and the suspension was stirred for one hour. A solution of 6.5 g of N'-(tertbutoxycarbonyl)-N-(chloroacetyl)-1,4-diamino-butane and 60 ml of dimethylformamide was slowly introduced. The reaction medium was stirred at 90° C. for 5 hours, then for 16 hours at ambient temperature. The suspension obtained was evaporated to dryness to obtain 13.08 g of a product which was chromatographed on silica and eluted with a hexane-ethyl acetate mixture (30-70) to obtain 4.98 g of the sought product melting at 132° C.

Workup

  1. stirringThe reaction medium was stirred at 90° C. for 5 hours
  2. waitfor 16 hours at ambient temperature
  3. customThe suspension obtained
  4. customwas evaporated to dryness

Sources & evidence

ORD record
ord-b4738c69ab8e44e493bf31e4fd4e5544
Source dataset
uspto-grants-1991_11
Patent number
US05064861

Reaction notes

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