Triethylamine → HCID 86658798, compound

HRID 2361944Notes

Reaction equation

HRID 2361944 reaction equation
ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[NH2:14][O:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[CH2:24]([N:26]([CH2:29]C)CC)[CH3:25]>ClCCl>[CH2:24]([NH:26][C:29](=[O:3])[NH:14][O:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 12919121tert-Butyl (aminooxy)acetate

Product 1

HCID 86658798HCID 86658798, compoundYield 138.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-nitrophenyl chloroformate (12.09 g, 60 mmol) in dichloromethane (200 ml) was stirred at 0° C. for 10 min. A solution of tert-butyl 2-(aminooxy)acetate (Compound XIV-5) (7.36 g, 50 mmol) in dichloromethane (100 ml) and triethylamine (9.06 ml, 65 mmol) were added and the mixture was stirred at room temperature for 0.5 hr. The reaction mixture was washed with water (300 ml) and brine (300 ml). The organic layer was dried over magnesium sulfate and filtered and the filtrate was concentrated in vacuo to give the desired product (15.14 g, 97%).

Workup

  1. washThe reaction mixture was washed with water (300 ml) and brine (300 ml)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c8bd418f5a1e4826877922afc1315429
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

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