Diethylamine → Boc-Dap N-palmityl-N-oleyl-amide

HRID 1050839Notes

Reaction equation

HRID 1050839 reaction equation
[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:22]([OH:24])=[O:23])[CH2:3][NH:4]C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[CH2:32]([N-:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56]/[CH:57]=[CH:58]\[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].C(NCC)C>ClCCl>[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:22]([OH:24])=[O:23])[CH2:3][NH2:4].[CH2:32]([N-:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56]/[CH:57]=[CH:58]\[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 131729180Boc-Dap(Fmoc) N-palmityl-N-oleyl-amide

Product 1

HCID 131729179Boc-Dap N-palmityl-N-oleyl-amideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g Boc-Dap(Fmoc)-N-palmityl-N-oleyl-amide raw product were dissolved in 8 ml anhydrous dichloromethane in a 50 ml round-bottom flask. 3 ml diethylamine were added and steered at room temperature (FIG. 4). Thin layer chromatography control of the reaction showed that after 4.5 hours the reaction of the starting product was completed. The volatile components were removed by a rotary evaporator and the residue is chromatography purified using 40 g silica gel 60 (Merck) using hexane/ethylacetate 5:1. The product was eluted using a step gradient consisting of ethylacetate, ethylacetate/methanol 4:1 and dichloromethane/methanol 4:1. 576 mg (0.85 mmol) Boc-Dap-N-palmityl-N-oleyl-amide were obtained as a yellow viscous oil.

Workup

  1. customsteered at room temperature
  2. customafter 4.5 hours
  3. customthe reaction of the starting product
  4. customThe volatile components were removed by a rotary evaporator
  5. custompurified
  6. washThe product was eluted

Sources & evidence

ORD record
ord-772e2e22540c4e61b283a064a2f55d32
Source dataset
uspto-grants-2016_07
Patent number
US09387262B2

Reaction notes

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