{4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-acetic acid → {4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-(2H-tetrazol-5-yl)-acetic acid

HRID 1356210Notes

Reaction equation

HRID 1356210 reaction equation
[C:1]([NH:9][C@H:10]([C:37](=[O:49])[NH:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:11][C:12]1[CH:36]=[CH:35][C:15]([O:16][CH:17]([C:21]2[N:22]=[N:23][N:24](C(C)(C3C=CC=CC=3)C)[N:25]=2)[C:18]([OH:20])=[O:19])=[CH:14][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[K])=O>CCO.[Pd]>[C:1]([NH:9][C@H:10]([C:37](=[O:49])[NH:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[CH2:11][C:12]1[CH:36]=[CH:35][C:15]([O:16][CH:17]([C:21]2[N:22]=[N:23][NH:24][N:25]=2)[C:18]([OH:20])=[O:19])=[CH:14][CH:13]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 69129259{4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-acetic acidHCID 178526052HCID 178526052, compound

Product 1

HCID 69129384{4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-(2H-tetrazol-5-yl)-acetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (40 mg) is added to a stirred slurry of {4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)--ethyl]-phenoxy}-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5- yl]-acetic acid of Step D (0.045 g, 0.068 mmol) and HCO2K (0.034 g, 0.409 mmol) in EtOH (2 mL). The reaction mixture is heated to reflux under N2. After 5 h, the reaction mixture is cooled to RT and filtered to remove Pd/C. The filtrate is diluted with EtOAc, water and 10% HCl and the layers separated. The organic layer is washed with 10% HCl and brine, dried (MgSO4) and concentrated under reduced pressure to provide {4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-(2H-tetrazol-5-yl )-acetic acid (compound 18); 1H NMR (400 MHz, acetone-d6) δ7.82 (m, 3H), 7.45 (m, 4H), 7.19 (m, 7H), 6.99 (d, 2H), 6.36 (s, 1H), 4.81 (m, 1H), 3.21 (m, 3H), 3.05 (m, 1H) 2.58 (t, 2H), 1.59 (m, 2H), 1.48 (m, 2H); MS (ES+) m/z 543 (M+1); MS (ES−) m/z 541 (M−1).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux under N2
  3. filtrationfiltered
  4. customto remove Pd/C
  5. additionThe filtrate is diluted with EtOAc, water and 10% HCl
  6. customthe layers separated
  7. washThe organic layer is washed with 10% HCl and brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9caef4f72b204b76b7868125f14c1c13
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

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