Hydrochloric Acid → Hydrochloric Acid

HRID 874783Notes

Reaction equation

HRID 874783 reaction equation
[ClH:1].[F:2][C:3]1[CH:4]=[C:5]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH:6]=[C:7]([O:10][CH2:11][C@H:12]([OH:28])[CH2:13][NH:14][C:15]([CH3:27])([CH3:26])[CH2:16][CH:17]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18]2)[C:8]=1[F:9].Cl.[CH2:35](O)[CH3:36]>C(OCC)C>[ClH:1].[CH2:35]([O:32][C:31](=[O:33])[CH2:30][CH2:29][C:5]1[CH:6]=[C:7]([O:10][CH2:11][C@H:12]([OH:28])[CH2:13][NH:14][C:15]([CH3:27])([CH3:26])[CH2:16][CH:17]2[CH2:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:25]2)[C:8]([F:9])=[C:3]([F:2])[CH:4]=1)[CH3:36].[ClH:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10345213Ronacaleret hydrochloride

Product 2

HCID 313Hydrochloric AcidHCID 10414041HCID 10414041, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of the propionic acid of Example 2 (2 g) in ethanol (20 mL) was added 2M HCl in diethyl ether (2 mL). The mixture was heated to reflux for 3 h. After cooling to RT, the resulting solution was concentrated to a yellow oil and dried under vacuum. The contents of the flask solidified to give the title compound as an HCl salt (2 g): 1H NMR (dmso-d6): δ 9.05 (m, 1H); 8.62 (m, 1H); 7.18 (m, 2H); 7.11 (m, 2H); 6.98 (app. d, J=7.1 Hz, 1H); 6.91 (m, 1H); 6.0 (br s, 1H); 4.27 (m, 1H); 4.14 (d, J=5.2 Hz, 2H); 4.06 (q, J=7.1 Hz, 2H); 3.18 (m, 1H); 3.09 (m, 2H); 2.98 (m, 1H); 2.82 (t, J=7.5 Hz, 2H); 2.61 (m, 5H); 1.97 (d, J=5.4 Hz, 2H); 1.39 (s, 6H); 1.17 (t, J=7.1 Hz, 3H): LCMS (m/z) M+H=476.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. concentrationthe resulting solution was concentrated to a yellow oil
  4. customdried under vacuum

Sources & evidence

ORD record
ord-3732805028ce4676ad08b7e939d8088b
Source dataset
uspto-grants-2015_03
Patent number
US08980950B2

Reaction notes

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