HCID 178435521, compound → HCID 178435519, compound

HRID 2211375Notes

Reaction equation

HRID 2211375 reaction equation
[CH3:1][C:2]([C:33]1[NH:37][N:36]=[N:35][N:34]=1)([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([O:16]CC2C=CC=CC=2)[C:13]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:12][C:11]=1[CH2:31][CH3:32])[CH3:3]>[Pd].C(O)C>[CH3:1][C:2]([C:33]1[NH:37][N:36]=[N:35][N:34]=1)([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([OH:16])[C:13]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)=[CH:12][C:11]=1[CH2:31][CH3:32])[CH3:3]

Participants

4

Reactant 1

HCID 178435521HCID 178435521, compound

Product 1

HCID 178435519HCID 178435519, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.1 g of 2-methyl-2-(1H-tetrazol-5-yl)-7-(2-ethyl-4-(4-fluorophenyl)-5-benzyloxyphenoxy)heptane, 1 g of 10% palladium on carbon, and 200 mL of ethanol was hydrogenated on a Parr™ apparatus at 35-40 psi for 2 hours. The mixture was filtered and the filtrate evaporated in vacuo. The residue was chromatographed on silica gel eluting with dichloromethane/methanol providing 750 mg (84%) of the desired title product. MS, NMR. Crystallization from diethyl ether/hexanes gave material with a melting point of 135°-137° C.; when crystallized from toluene, the melting point was 142°-143° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated in vacuo
  3. customThe residue was chromatographed on silica gel eluting with dichloromethane/methanol providing 750 mg (84%) of the desired title product
  4. customCrystallization from diethyl ether/hexanes
  5. customgave material with a melting point of 135°-137° C.
  6. customwhen crystallized from toluene

Sources & evidence

ORD record
ord-f8710d1e117f400a8b85b90b04d02e3c
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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