Hydrochloric Acid → HCID 68752507, compound

HRID 881852Notes

Reaction equation

HRID 881852 reaction equation
C([O:3][C:4](=[O:32])[C@@H:5]([CH3:31])[CH2:6][CH:7]([NH:23][C:24](=[O:30])[CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[CH:11][CH:10]=1)C.[OH-].[Na+].Cl>>[C:27]([CH2:26][CH2:25][C:24]([NH:23][CH:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[CH:11][CH:10]=1)[CH2:6][C@H:5]([CH3:31])[C:4]([OH:32])=[O:3])=[O:30])([OH:29])=[O:28]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68753820HCID 68753820, compound

Product 1

HCID 68752507HCID 68752507, compound

Procedure

To (S)-4-(3-carboxy-propionylamino)-5-(2′-methoxy-biphenyl-4-yl)-2-methyl-pentanoic acid ethyl ester was added 1M NaOH (2 ml) and stirred at room temperature for 2 hours. Then, to the mixture was added 2 ml of 1M HCl and concentrated under reduced pressure. The obtained residue was purified by RP-HPLC (H2O (0.1% TFA)/CH3CN) to afford 110 mg of white powder. HPLC Retention time 0.86 minutes (condition A): MS 414.1 (M+1) 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99-1.06 (m, 3 H) 1.28-1.48 (m, 1 H) 1.66-1.84 (m, 1 H) 2.24-2.39 (m, 5 H) 2.63-2.75°(m, 2 H) 3.75-4.02 (m, 4 H) 6.97-7.04 (m, 1 H) 7.09 (d, J=7.58 Hz, 1 H) 7.16-7.22 (m, 2 H) 7.24-7.29 (m, 1 H) 7.29-7.35 (m, 1 H) 7.35-7.41 (m, 2 H) 7.77 (d, J=8.59 Hz, 1 H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe obtained residue was purified by RP-HPLC (H2O (0.1% TFA)/CH3CN)

Sources & evidence

ORD record
ord-6e9030d6f18c40af9c2d1c3fe95ff5a2
Source dataset
uspto-grants-2015_03
Patent number
US08993631B2

Reaction notes

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