HCID 70113844, compound → HCID 178525229, compound

HRID 333313Notes

Reaction equation

HRID 333313 reaction equation
[C:1]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:18][C:19]([C:21]2([CH2:26][C:27]([O:29]CC3C=CC=CC=3)=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[C:9]2[N:13](CCC#N)[N:12]=[N:11][N:10]=2)=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@H:8]([NH:18][C:19]([C:21]2([CH2:26][C:27]([OH:29])=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[C:9]2[NH:13][N:12]=[N:11][N:10]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 70113844HCID 70113844, compound

Product 1

HCID 178525229HCID 178525229, compoundYield 8.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-benzyl 2-(1-(2-(biphenyl-4-yl)-1-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate (39 mg, 0.069 mmol) in MeOH (6 mL) was hydrogenated in H-Cube (Cartridge; 10% Pd/C) at room temperature for 0.5 hour. The reaction mixture was concentrated in vacuo. This was treated with 2M NaOH aqueous solution (1 mL) and MeOH (1 mL) and stirred for 0.5 hour. The reaction mixture was acidified with 1M HCl and the mixture was purified by reverse phase HPLC (column; Sunfire C-18, eluent; 0.1% TFA-H2O/CH3CN) to give {1-[(S)-2-biphenyl-4-yl-1-(1H-tetrazol-5-yl)-ethylcarbamoyl]-cyclopentyl}-acetic acid (2.5 mg). LCMS (condition C): 420 (M+1); retention time=1.70 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36-1.54 (m, 6H), 1.87-1.98 (m, 2H), 2.59 (s, 3H), 2.59 (s, 2H), 3.22-3.66 (m, 2H), 5.39-5.48 (m, 1H), 7.29-7.37 (m, 3H), 7.44 (t, J=8.08 Hz, 2H), 7.55 (t, J=8.34 Hz, 2H), 7.59-7.64 (m, 2H), 8.17 (d, J=8.08 Hz, 1H); HRMS (ES+) m/z for C23H25N5O3 [M+H]+ calcd 419.2. found 419.2

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThis was treated with 2M NaOH aqueous solution (1 mL) and MeOH (1 mL)
  3. customthe mixture was purified by reverse phase HPLC (column; Sunfire C-18, eluent; 0.1% TFA-H2O/CH3CN)

Sources & evidence

ORD record
ord-f3a0c1e03acd490c96ba66c76d991b70
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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