HCID 86754301, compound → HCID 15858099, compound

HRID 583177Notes

Reaction equation

HRID 583177 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:33][CH2:32][C@:7]2([O:11][CH2:10][CH:9]([C:12]3[C:20]4[N:19]=[CH:18][N:17](C(OC(C)(C)C)=O)[C:16]=4[CH:15]=[C:14]([C:28]([F:31])([F:30])[F:29])[CH:13]=3)[CH2:8]2)[C@@H:6]1[C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)=[O:4]>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[CH3:1][O:2][C:3]([C@H:5]1[CH2:33][CH2:32][C@:7]2([O:11][CH2:10][CH:9]([C:12]3[C:20]4[N:19]=[CH:18][NH:17][C:16]=4[CH:15]=[C:14]([C:28]([F:31])([F:29])[F:30])[CH:13]=3)[CH2:8]2)[C@@H:6]1[C:34]1[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=1)=[O:4]

Participants

4

Reactant 1

HCID 86754301HCID 86754301, compound

Product 1

HCID 15858099HCID 15858099, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (5R, 6S, 7S)-6-(4-fluorophenyl)-3-[1-(tert-butyloxycarbonyl)-6-trifluoromethyl-benzimidazol-4-yl)-1-oxaspiro[4.4]nonane-7-carboxylic acid methyl ester (13.5 mg, 0.024 mmol) in methylene chloride (1 mL) was treated with anhydrous zinc bromide (11 mg, 0.049 mmol) for 6 hours at room temperature. The reaction was quenched with saturated NaHCO3 solution, diluted with methylene chloride, the organic layer separated and washed with saturated brine solution, dried (Na2SO4), and evaporated to obtain 8.4 mg of the title compound. 400 MHz 1H NMR (CD3OD): δ 1.92-2.11 (m, 3H), 2.24-2.37 (m, 2H), 2.48 (dd, 1H), 3.13 (m, 1H), 3.41 (m, 1H), 3.56 (s, 3H), 4.17 (t, 1H), 6.75 (br s, 1H), 7.06 (t, 2H), 7.42 (m, 2H), 7.68 (br s, 1H), 8.28 (br s, 1H); Mass spec (NH3 /CI): δ 414 (M+1).

Workup

  1. customThe reaction was quenched with saturated NaHCO3 solution
  2. additiondiluted with methylene chloride
  3. customthe organic layer separated
  4. washwashed with saturated brine solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-5d029b0e6e8646d9a9dca26c17bc53e6
Source dataset
uspto-grants-1999_07
Patent number
US05929094

Reaction notes

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