Triethylamine → HCID 86718995, compound

HRID 1746278Notes

Reaction equation

HRID 1746278 reaction equation
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[NH:15][NH2:16].CCN(CC)CC.[CH2:28]([O:31][CH:32]([CH2:35][O:36][CH2:37][C:38]#[CH:39])[CH2:33][NH2:34])[C:29]#[CH:30]>C1COCC1.O>[CH2:28]([O:31][CH:32]([CH2:35][O:36][CH2:37][C:38]#[CH:39])[CH2:33][NH:34][C:2]([NH:16][NH:15][C:14]([O:18][CH2:19][CH3:20])=[O:17])=[O:3])[C:29]#[CH:30]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 821294-Nitrophenyl chloroformateHCID 86718993HCID 86718993, compound

Product 1

HCID 86718995HCID 86718995, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To 4-nitrophenyl chloroformate (1084 mg, 5.38 mmol) in THF (18 mL) at 0° C. was added ethyl carbazate (560 mg, 5.38 mmol) and Et3N (2.98 mL, 21.52 mmol). The mixture was stirred at 0° C. for 1 h. Then more Et3N (2.98 mL, 21.52 mmol) was added, followed by a solution of 2,3-bis(prop-2-ynyloxy)propan-1-amine (I-13b: 5.92 mmol) in 5 mL THF, and the mixture was stirred at room temperature for 30 min. 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), giving ethyl 2-(2,3-bis(prop-2-ynyloxy)propylcarbamoyl)hydrazinecarboxylate (I-13c: 855 mg, 54%) as a light yellow oil. LC-MS (M+1) 298.2, t=0.75 minute.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. extractionextracted twice with AcOEt
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography (40-100% AcOEt/heptane)

Sources & evidence

ORD record
ord-27b7d91f7b1a4fe0a419a8d6a17a8a06
Source dataset
uspto-grants-2015_10
Patent number
US09149541B2

Reaction notes

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