Triethylamine hydrochloride → HCID 90192604, compound

HRID 923509Notes

Reaction equation

HRID 923509 reaction equation
[C:1]([C@:3]1([CH3:17])[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])#[N:2].Cl.C(N(CC)CC)C.[N-:26]=[N+:27]=[N-:28].[Na+]>C1(C)C=CC=CC=1>[CH3:8][C:5]1([CH3:9])[N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@:3]([CH3:17])([C:1]2[N:26]=[N:27][NH:28][N:2]=2)[CH2:7][O:6]1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 90192607HCID 90192607, compound

Product 1

HCID 90192604HCID 90192604, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
103 °C

Procedure

To a mixture of 6.96 g of tert-butyl (4R)-4-cyano-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate, 12.5 g of triethylamine hydrochloride, and 105 ml of toluene was added 5.84 g of sodium azide, followed by stirring at 103° C. for 3 hours. The insoluble materials were separated by filtration and the filtrate was concentrated. The obtained residue was purified twice by silica gel column chromatography to obtain 7.65 g of tert-butyl (4R)-2,2,4-trimethyl-4-(2H-tetrazol-5-yl)-1,3-oxazolidine-3-carboxylate.

Workup

  1. customThe insoluble materials were separated by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe obtained residue was purified twice by silica gel column chromatography

Sources & evidence

ORD record
ord-cde14edee73b4254bab4c85390f8259b
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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