(S)-benzyl 2-(1-(2-(3'-methylbiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate → HCID 178424509, compound

HRID 333299Notes

Reaction equation

HRID 333299 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:21][C:22]([C:24]3([CH2:29][C:30]([O:32]CC4C=CC=CC=4)=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:23])[C:16]3[NH:20][N:19]=[N:18][N:17]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:21][C:22]([C:24]3([CH2:29][C:30]([OH:32])=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:23])[C:16]3[NH:17][N:18]=[N:19][N:20]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 178424508(S)-benzyl 2-(1-(2-(3'-methylbiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate

Product 1

HCID 178424509HCID 178424509, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-benzyl 2-(1-(2-(3′-methylbiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate (175 mg, 0.334 mmol) was hydrogenated with 5% Pd—C (35.6 mg) in MeOH at room temperature for 0.5 hours. The reaction mixture was filtered through celite pad, and the filtrate was concentrated under reduced pressure. The residue was purified by reverse phase HPLC (Waters SunFire C-18 column, 0.1% TFA in H2O/CH3CN) to give (S)-2-(1-(2-(3′-methylbiphenyl-4-yl)-1-(1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetic acid. Retention time=0.76 minutes (condition B); MS (m+1)=434; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33-1.54 (m, 6H), 1.87-2.01 (m, 2H), 2.36 (s, 3H), 2.59 (s, 2H), 3.22-3.77 (m, 2H), 5.43 (dd, J=8.34, 14.91 Hz, 1H), 7.15 (d, J=7.33 Hz, 1H), 7.27-7.35 (m, 3H), 7.38-7.45 (m, 2H), 7.53 (d, J=8.08 Hz, 2H), 8.16 (d, J=7.83 Hz, 1H); HRMS (ES+) m/z for C24H27N5O3 [M+H]+ calcd 433.2. found 433.2

Workup

  1. filtrationThe reaction mixture was filtered through celite pad
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by reverse phase HPLC (Waters SunFire C-18 column, 0.1% TFA in H2O/CH3CN)

Sources & evidence

ORD record
ord-71af631bc1524ad79cb9802e87d566be
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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