Tributyltin azide → cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl 3-(1H-tetrazol-5-yl)benzoate

HRID 858196Notes

Reaction equation

HRID 858196 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=1)[C:6]([O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])[CH2:10]1)=[O:7])#[N:2].C([Sn]([N:46]=[N+:47]=[N-:48])(CCCC)CCCC)CCC>C1(C)C(C)=CC=CC=1>[NH:46]1[C:1]([C:3]2[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=2)[C:6]([O:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][CH2:16][C:17]3[N:18]=[C:19]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)[O:20][C:21]=3[CH3:22])[CH2:10]2)=[O:7])=[N:2][N:48]=[N:47]1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 69655148cis-3-[2-(4-Fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl 3-cyanobenzoate

Product 1

HCID 178434850cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl 3-(1H-tetrazol-5-yl)benzoate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
160 °C

Procedure

0.06 g of cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl 3-cyanobenzoate is dissolved in 5 ml of xylene, 150 μm of tributyltin azide are added and the mixture is heated under reflux at 160° C. for 24 hours. The reaction is terminated by addition of 1 ml of trifluoroacetic acid (in 1 ml of methanol), 3 ml of water are added and the mixture is extracted with ethyl acetate (2×10 ml). The combined organic phases are washed with saturated sodium chloride solution and dried over magnesium sulfate, and the solvent is then removed under reduced pressure. Purification by preparative HPLC gives 0.04 g of the desired cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl 3-(1H-tetrazol-5-yl)benzoate as an amorphous solid.

Workup

  1. temperaturethe mixture is heated
  2. customThe reaction is terminated by addition of 1 ml of trifluoroacetic acid (in 1 ml of methanol), 3 ml of water
  3. additionare added
  4. extractionthe mixture is extracted with ethyl acetate (2×10 ml)
  5. washThe combined organic phases are washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent is then removed under reduced pressure
  8. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-5ee19fe33fe84d0f8f2e0bbb7f8c5439
Source dataset
uspto-grants-2006_12
Patent number
US07148246B2

Reaction notes

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