Water → HCID 68095250, compound

HRID 2173342Notes

Reaction equation

HRID 2173342 reaction equation
[CH:1](OCC)(OCC)OCC.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:22])[C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1.[N-:23]=[N+:24]=[N-:25].[Na+].O>C(O)(=O)C>[N:11]1([C:12]2[CH:13]=[CH:14][C:15]([CH:18]([CH3:22])[C:19]([OH:21])=[O:20])=[CH:16][CH:17]=2)[CH:1]=[N:25][N:24]=[N:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 430264-Aminohydratropic acid

Product 1

HCID 68095250HCID 68095250, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Triethyl orthoformate (5.29 ml, 31.8 mmol) and 2-(4-aminophenyl) propionic acid (3.26 g, 19.73 mmol) were suspended in acetic acid (50 ml) then added sodium azide (1.924 g, 29.6 mmol). The mixture was refluxed for 3 hours then let stirred at room temperature overnight. The reaction was poured into water (60 ml) and extracted with ethyl acetate (60 ml). The organic layer was separated and dried over MgSO4. The mixture was filtered and concentrated to yield 2-[4-(1H-tetrazol-1yl)phenyl]propanoic acid (4.2 g, 98%). LC-MS (IE, m/z): 219 [M+1]+.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. extractionextracted with ethyl acetate (60 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-24635438b4584e5fa19c286520a2bea1
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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