Ethanol hydrochloride → Hydrochloric Acid

HRID 541498Notes

Reaction equation

HRID 541498 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@H:4]([OH:30])[CH2:5][N:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=2[F:29])=[CH:18][CH:17]=1)[NH:7]C(OC(C)(C)C)=O.[ClH:32].[CH3:33]CO>>[CH2:1]([O:2][C:3](=[O:31])[C@H:4]([OH:30])[CH2:5][N:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=2[F:29])=[CH:18][CH:17]=1)[NH2:7])[CH3:33].[ClH:32]

Participants

4

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 86705084(R)-3-[N'-t-butoxycarbonyl-N-(5'-chloro-2'-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic acid methyl ester

Product 2

HCID 313Hydrochloric AcidHCID 67972425(R)-3-[N-(5'-Chloro-2'-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic Acid Ethyl Ester

Procedure

A solution of (R)-3-[N′-t-butoxycarbonyl-N-(5′-chloro-2′-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic acid methyl ester (20 g, 16 mmol) in HCl/EtOH (1.1 M, 200 mL) was stirred overnight and then concentrated in vacuo. The residue was dispersed in EtOAc (2×40 mL), and the precipitate was collected by filtration to give the title compound as an off-white solid HCl salt (8.8 g). LC-MS: 367 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ 1.05 (t, J=7.2 Hz, 3H), 3.05-3.03 (q, J=7.2 Hz, 2H), 4.06-3.95 (m, 4H), 4.42 (br, 1H), 6.46 (br, 1H), 7.62-7.40 (m, 7H), 9.42 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was dispersed in EtOAc (2×40 mL)
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-9226d9d05826404499111eaf38c54d1a
Source dataset
uspto-grants-2014_10
Patent number
US08871792B2

Reaction notes

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