HCID 178472562, compound → HCID 178525818, compound

HRID 331669Notes

Reaction equation

C([O:3][C:4](=[O:39])[C@@H:5]([NH:15][C@H:16]([C:31](=[O:38])[NH:32][C:33]1[NH:37][N:36]=[N:35][N:34]=1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)=[CH:20][CH:19]=1)[CH2:6][O:7]CC1C=CC=CC=1)C>CCOC(C)=O.CCO.[Pd]>[Cl:30][C:26]1[CH:25]=[C:24]([C:21]2[CH:20]=[CH:19][C:18]([CH2:17][C@H:16]([NH:15][C@@H:5]([CH2:6][OH:7])[C:4]([OH:39])=[O:3])[C:31](=[O:38])[NH:32][C:33]3[NH:37][N:36]=[N:35][N:34]=3)=[CH:23][CH:22]=2)[CH:29]=[CH:28][CH:27]=1.[C:21]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:20]=[CH:19][C:18]([CH2:17][C@H:16]([NH:15][C@@H:5]([CH2:6][OH:7])[C:4]([OH:39])=[O:3])[C:31](=[O:38])[NH:32][C:33]2[NH:34][N:35]=[N:36][N:37]=2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (S)-3-benzyloxy-2-[(S)-2-(3′-chloro-biphenyl-4-yl)-1-(1H-tetrazol-5-ylcarbamoyl)-ethylamino]-propionic acid ethyl ester (47 mg, 0.090 mmol) in EtOAc (1 mL) and EtOH (1 mL) was added 5% Pd—C (9.6 mg, 0.0045 mmol). H2 gas was loaded with a balloon and the reaction mixture was stirred at 50° C. for 6 hours. The reaction mixture was filtered through celite pad and the filtrate was concentrated. The residue was purified by reverse phase HPLC (Sunfire C-18 column, eluent: 0.1% TFA in H2O/CH3CN) to give (S)-2-[(S)-2-(3′-chloro-biphenyl-4-yl)-1-(1H-tetrazol-5-ylcarbamoyl)-ethylamino]-3-hydroxy-propionic acid and (S)-2-[(S)-2-biphenyl-4-yl-1-(1H-tetrazol-5-ylcarbamoyl)-ethylamino]-3-hydroxy-propionic acid.

Workup

filtrationThe reaction mixture was filtered through celite pad
concentrationthe filtrate was concentrated
customThe residue was purified by reverse phase HPLC (Sunfire C-18 column, eluent: 0.1% TFA in H2O/CH3CN)

Sources & evidence

ORD record: ord-5dd961d016ed49e788a403ef5c31106e
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877786B2

Reaction notes

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