Triethylamine → HCID 86718998, compound

HRID 1746284Notes

Reaction equation

HRID 1746284 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=CC([N+]([O-])=O)=CC=1)=[O:3].[C:14](OCC)(=[O:17])[NH:15][NH2:16].CCN(CC)CC.[N:28]([CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][NH2:42])=[N+:29]=[N-:30]>C1COCC1.O>[N:28]([CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][NH:42][C:14](=[O:17])[NH:15][NH:16][C:2]([O:4][CH2:5][CH3:10])=[O:3])=[N+:29]=[N-:30]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 821294-Nitrophenyl chloroformateHCID 27352801-Amino-11-azido-3,6,9-trioxaundecane

Product 1

HCID 86718998HCID 86718998, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To 4-nitrophenyl chloroformate (1008 mg, 5.00 mmol) in THF (17 mL) at 0° C. was added ethyl carbazate (0.521 g, 5 mmol) and Et3N (2.08 mL, 15.00 mmol). The mixture was stirred at 0° C. for 30 min. Then a solution of 11-azido-3,6,9-trioxaundecan-1-amine (1.09 ml, 5.50 mmol) in 2 mL THF, and the mixture was stirred at room temperature for 16 h. Water was added, extracted twice with AcOEt, dried over MgSO4, filtered, and concentrated. The crude product was purified by silica gel chromatography (40-100% AcOEt/heptane, then 5% MeOH/AcOEt), giving ethyl 16-azido-4-oxo-8,11,14-trioxa-2,3,5-triazahexadecan-1-oate (I-18a: 1.23 g, 71%) as a colorless oil. LC-MS (M+1) 349.4, t=1.63 minute.

Workup

  1. extractionextracted twice with AcOEt
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (40-100% AcOEt/heptane

Sources & evidence

ORD record
ord-fd36a5ea0bc343f9a5901158e72c17e2
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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