Triethylamine → HCID 86760442, compound

HRID 351144Notes

Reaction equation

HRID 351144 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C:11]2[CH:12]=[C:13]([C:16]([OH:18])=O)[CH:14]=[CH:15][C:10]=2[O:9][CH:8]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[N-:32]=[N+:33]=[N-:34].[Na+]>CC(C)=O.O>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C:11]2[CH:12]=[C:13]([C:16]([N:32]=[N+:33]=[N-:34])=[O:18])[CH:14]=[CH:15][C:10]=2[O:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 69410961HCID 69410961, compound

Product 1

HCID 86760442HCID 86760442, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

The acid (1 mmol) obtained in Step A is dissolved in acetone. The temperature of the reaction mixture is lowered with the aid of an ice bath, and triethylamine (1.5 mmol) and then ethyl chloroformate (1.5 mmol) are added. After stirring for 15 minutes, sodium azide (1.5 mmol), previously dissolved in water (1 ml of water per 400 mg of sodium azide), is added and stirring is again carried out for 10 minutes. The mixture is extracted with ethyl acetate, and the organic phase is then washed with water, dried over magnesium sulphate and evaporated to dryness. The azide obtained is used, without additional purification, in the following Step.

Workup

  1. customThe temperature of the reaction mixture is lowered with the aid of an ice bath
  2. additionis added
  3. stirringstirring
  4. waitis again carried out for 10 minutes
  5. extractionThe mixture is extracted with ethyl acetate
  6. washthe organic phase is then washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-c7ab31f8ac0b4bb4b5ef00b1b03df1aa
Source dataset
uspto-grants-2007_02
Patent number
US07183318B2

Reaction notes

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