[4-(5-{3-[3-(4-Fluorophenyl)prop-1-ynyl]phenyl}tetrazol-2-ylmethyl)phenoxy]acetic acid tert-butyl ester → [4-(5-{3-[3-(4-Fluorophenyl)prop-1-ynyl]phenyl}tetrazol-2-ylmethyl)phenoxy]acetic acid

HRID 349459Notes

Reaction equation

HRID 349459 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[N:20]=[N:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[C:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)[CH:22]=3)=[N:17]2)=[CH:11][CH:10]=1)(C)(C)C>FC(F)(F)C(O)=O>[F:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][C:28]#[C:27][C:23]2[CH:22]=[C:21]([C:18]3[N:19]=[N:20][N:16]([CH2:15][C:12]4[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]([OH:37])=[O:5])=[CH:14][CH:13]=4)[N:17]=3)[CH:26]=[CH:25][CH:24]=2)=[CH:31][CH:32]=1

Participants

3

Reactant 1

HCID 68980311[4-(5-{3-[3-(4-Fluorophenyl)prop-1-ynyl]phenyl}tetrazol-2-ylmethyl)phenoxy]acetic acid tert-butyl ester

Product 1

HCID 68976960[4-(5-{3-[3-(4-Fluorophenyl)prop-1-ynyl]phenyl}tetrazol-2-ylmethyl)phenoxy]acetic acidYield 62.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [4-(5-{3-[3-(4-fluorophenyl)prop-1-ynyl]phenyl}tetrazol-2-ylmethyl) phenoxy]-acetic acid tert-butyl ester (0.19 g. 0.38 mmol) in trifluoroacetic acid (“TFA”) (6 mL) was stirred at room temperature for 75 minutes, then evaporated to dryness. The residue was triturated with ether, evaporated, triturated again with ether/hexanes, evaporated, then triturated with hexanes/ethyl acetate 3:1. The solid was collected by filtration, washed with hexanes/ethyl acetate 3:1 and dried to give 0.1047 g of orange solid (59.11% yield).

Workup

  1. customevaporated to dryness
  2. customThe residue was triturated with ether
  3. customevaporated
  4. customtriturated again with ether/hexanes
  5. customevaporated
  6. customtriturated with hexanes/ethyl acetate 3:1
  7. filtrationThe solid was collected by filtration
  8. washwashed with hexanes/ethyl acetate 3:1
  9. customdried

Sources & evidence

ORD record
ord-67c5783a191b4f128e1ec39688a5a56f
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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