Acetic Acid → HCID 57652729, compound

HRID 1013266Notes

Reaction equation

HRID 1013266 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:4].[N-:20]=[N+:21]=[N-:22].[Na+].[CH3:24]C(O)=O>COC(OC)OC>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH:8]=[C:9]([N:11]2[CH:24]=[N:22][N:21]=[N:20]2)[CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 33557Sodium AzideHCID 57652724HCID 57652724, compound

Product 1

HCID 57652729HCID 57652729, compound

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

To a suspension of 5-amino-2′-methoxy-biphenyl-3-carboxylic acid methyl ester (7.2 g, 28 mmol) in trimethoxymethane (22.8 mL) was added NaN3 (5.7 g) followed by HOAc (285 mL). The reaction mixture was stirred at room temperature for 30 minutes, then stirred at 100° C. for three hours, and then stirred at room temperature for 18 hours. The resulting mixture was partitioned between water and methylene chloride, and the combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated under reduced pressure to give 8.6 g of 2′-methoxy-5-tetrazol-1-yl-biphenyl-3-carboxylic acid methyl ester, MS (M+H)=311.

Workup

  1. stirringstirred at 100° C. for three hours
  2. stirringstirred at room temperature for 18 hours
  3. customThe resulting mixture was partitioned between water and methylene chloride
  4. washthe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dcd24a309df649e3aa4afcb2eba6e023
Source dataset
uspto-grants-2011_07
Patent number
US07981914B2

Reaction notes

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