tert-butyl N-(4-aminobutyl)carbamate → N-(tert-butoxycarbonyl)-N'-(1-naphthyl acetyl)-1,4-diamino-butane

HRID 973729Notes

Reaction equation

HRID 973729 reaction equation
[C:1]1([CH2:11][C:12](Cl)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:15]([O:19][C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][NH2:27])=[O:21])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:15]([O:19][C:20]([NH:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:12](=[O:13])[CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 8471TriethylamineHCID 27953862-(Naphthalen-1-yl)acetyl chloride

Product 1

HCID 19989015N-(tert-butoxycarbonyl)-N'-(1-naphthyl acetyl)-1,4-diamino-butaneYield 97.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 16.3 g of 1-naphthyl-acetic acid chloride in 80 ml of chloroform was added at +10° C. to a solution cooled to +10° C. of 15 g of N-(tert-butoxycarbonyl)-1,4-diamino butane, 100 ml of chloroform and 14 ml of triethylamine and after one hour of stirring at ambient temperature, the mixture was concentrated to dryness under reduced pressure. The residue was taken up in water, separated and dried under reduced pressure at 50° C. to obtain 27.8 g of the expected product.

Workup

  1. concentrationthe mixture was concentrated to dryness under reduced pressure
  2. customseparated
  3. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-62f119eefb404bb29accddb1e10d90ea
Source dataset
uspto-grants-1991_11
Patent number
US05064861

Reaction notes

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