HCID 68688738, compound → HCID 68687354, compound

HRID 1991402Notes

Reaction equation

HRID 1991402 reaction equation
C([O:8][C:9](=[O:37])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]=[C:19]([C@H:21]3[CH2:26][CH2:25][CH2:24][CH2:23][N:22]3[C:27](=[O:36])[CH2:28][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:18][N:17]=2)=[CH:12][CH:11]=1)C1C=CC=CC=1>CO.[Pd]>[O:29]([CH2:28][C:27]([N:22]1[CH2:23][CH2:24][CH2:25][CH2:26][C@@H:21]1[C:19]1[O:18][N:17]=[C:16]([C:13]2[CH:14]=[CH:15][C:10]([C:9]([OH:37])=[O:8])=[CH:11][CH:12]=2)[N:20]=1)=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 1

HCID 68688738HCID 68688738, compound

Product 1

HCID 68687354HCID 68687354, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4 mmol of (R)-4-{5-[1-(2-Phenoxy-acetyl)-piperidin-2-yl]-[1,2,4]oxadiazol-3-yl}-benzoic acid benzyl ester were dissolved in MeOH and treated with Pd/C and flushed with hydrogen (3 bar) and stirred for 30 min. The catalyst was filtered off and the solvent evaporated. After extraction from ethylacetate/water the resulting oil was purified via preperative HPLC. The corresponding alkylesters were treated with aq. 2N NaOH or LiOH in methanol at room temperature. The allylester can be cleaved using Pd(Ph3)4 as catalyst and morpholine as a nucleophile.

Workup

  1. customflushed with hydrogen (3 bar)
  2. filtrationThe catalyst was filtered off
  3. customthe solvent evaporated
  4. extractionAfter extraction from ethylacetate/water the resulting oil
  5. customwas purified via preperative HPLC
  6. additionThe corresponding alkylesters were treated with aq. 2N NaOH or LiOH in methanol at room temperature

Sources & evidence

ORD record
ord-ab871db56b0c415ead99948f3b95f909
Source dataset
uspto-grants-2010_01
Patent number
US07645776B2

Reaction notes

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