Sodium Azide → HCID 19377651, compound

HRID 2210884Notes

Reaction equation

HRID 2210884 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:34])[CH:15]([C:17]1[N:18]=[N:19][N:20]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[N:21]=1)Br)([CH3:3])[CH3:2].[N-:35]=[N+]=[N-].[Na+].[BH4-].[Na+]>C(O)C.C(OCC)(=O)C>[NH2:35][CH:15]([C:17]1[N:18]=[N:19][N:20]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[N:21]=1)[C:14]([NH:13][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:10]([CH3:12])[CH3:11])=[O:34]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 4311764Sodium borohydrideHCID 15296921HCID 15296921, compound

Product 1

HCID 19377651HCID 19377651, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
24 °C

Procedure

(±)-N-(2,6-diisopropylphenyl)-2-(2-dodecyl -2H-tetrazol-5-yl)-2-bromoacetamide (1 g, 1.87 mmol) from Example 1 (e) was added to a solution containing sodium azide (0.24 g, 3.7 mmol) in ethanol (20 mL). The solution was stirred for 72 hours at 24° C. Sodium borohydride (0.07 g, 1.87 mmol) was added to the reaction mixture in one portion. The suspension was stirred for 12 hours at 24° C., then concentrated in vacuo. The resulting residue was triturated with ethyl acetate, filtered, and the filtrate was concentrated in vacuo leaving a viscous liquid. The liquid was dissolved in 10 mL of 50% ethyl acetate/ 50% hexane and purified by silica gel chromatography (elution with 50% ethyl acetate/50% hexane) to give (±)-2-amino-N-(2,6-diisopropylphenyl)-2-(2-dodecyl -2H-tetrazol-5-yl)-acetamide (0.58 g, 66%) as a colorless liquid;

Workup

  1. stirringThe suspension was stirred for 12 hours at 24° C.
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was triturated with ethyl acetate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customleaving a viscous liquid
  7. custompurified by silica gel chromatography (elution with 50% ethyl acetate/50% hexane)

Sources & evidence

ORD record
ord-0c19ab5d7ec1402fa2e0ede9263848d3
Source dataset
uspto-grants-1995_10
Patent number
US05461049

Reaction notes

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