Diethylamine → HCID 131729183, compound

HRID 2273585Notes

Reaction equation

HRID 2273585 reaction equation
[NH:1]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:2]([C:25]([OH:27])=[O:26])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[CH2:35]([N-:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].C(NCC)C>ClCCl>[NH:1]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:2]([C:25]([OH:27])=[O:26])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH2:35]([N-:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 131729184HCID 131729184, compound

Product 1

HCID 131729183HCID 131729183, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.377 g Boc-Lys(Fmoc)-N-lauryl-N-myristyl-amide were dissolved in 16 ml anhydrous dichloromethane in a 50 ml round-bottom flask. 6 ml diethylamine were added and the mixture was stirred at room temperature for 5 hours (FIG. 8). The volatile components were removed using a rotary evaporator and the residue was purified by chromatography using 40 g silica gel 60 (Merck) with hexane/ethylacetate 5:1. The product was eluted using a step gradient consisting of ethylacetate, dichloromethane and dichloromethane/methanol 3:1. 556 mg (0.911 mmol) Boc-Lys-N-lauryl-N-myristyl amide was obtained as yellowish viscous oil as well as 119 mg of a mixed fraction.

Workup

  1. customThe volatile components were removed
  2. customa rotary evaporator
  3. customthe residue was purified by chromatography
  4. washThe product was eluted

Sources & evidence

ORD record
ord-a847a90722b143fab539a8f93a7760cc
Source dataset
uspto-grants-2015_09
Patent number
US09125820B2

Reaction notes

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