Hydrochloric Acid → (2R,4S)-4-(3-carboxy-propionylamino)-5-(3'-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid
Reaction equation
C([O:3][C:4](=[O:31])[C@H:5]([CH3:30])[CH2:6][C@H:7]([NH:22][C:23](=[O:29])[CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:11][CH:10]=1)C.[OH-].[Na+].Cl>CCO>[C:26]([CH2:25][CH2:24][C:23]([NH:22][C@H:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:11][CH:10]=1)[CH2:6][C@@H:5]([CH3:30])[C:4]([OH:31])=[O:3])=[O:29])([OH:28])=[O:27]Participants
Procedure
To a stirred solution of (2R,4S)-4-(3-carboxy-propionylamino)-5-(3′-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid ethyl ester (20 mg, 0.045 mmol) in 2 ml EtOH was added 1 ml of aqueous 1M NaOH and the solution was stirred for an hour. The reaction mixture was acidified to pH=2 to 3 with aqueous 1M HCl. Solvent was removed under reduced pressure and the residue was purified by RP-HPLC to give 10 mg (2R,4S)-4-(3-carboxy-propionylamino)-5-(3′-chloro-biphenyl-4-yl)-2-methyl-pentanoic acid. LC/MS m/z 418.3 (M+H), 419.4 (M−H). LC/MS (Condition A): 1.21 min. 1H NMR (400 MHz, DMSO-d6): 1.04-1.05 (d, J=7.07 Hz, 3H), 1.30-1.37 (m, 1H), 1.73-1.80 (m, 1H), 2.24-2.39 (m, 5H), 2.66-2.73 (m, 2H), 3.90-3.98 (m, 1H), 7.25-7.27 (d, J=8.08 Hz, 2H), 7.39-7.41 (m, 1H), 7.45-7.49 (t, J=7.83 Hz, 1H), 7.60-7.64 (m, 3H), 7.70-7.71 (t, J=2.02 Hz, 1H), 7.75-7.77 (d, J=8.59 Hz, 1H), 12.04 (br s, 2H).
Workup
- customSolvent was removed under reduced pressure
- customthe residue was purified by RP-HPLC
Sources & evidence
- ORD record
- ord-34a5fc892ba24fd58012f6c90d2b6d10
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993631B2
Reaction notes
Loading…