Hydrochloric Acid → (S)-methyl 2-amino-3-(3-bromo-5-fluorophenyl)propanoate hydrochloride

HRID 1471647Notes

Reaction equation

HRID 1471647 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([F:22])[CH:21]=1)[CH2:5][C@H:6]1[C:11]([O:12][CH3:13])=N[C@H](C(C)C)C(OC)=[N:7]1.[ClH:23].[OH-:24].[Na+]>C(#N)C>[ClH:23].[NH2:7][C@@H:6]([CH2:5][C:4]1[CH:19]=[C:20]([F:22])[CH:21]=[C:2]([Br:1])[CH:3]=1)[C:11]([O:12][CH3:13])=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90280221(2S,5R)-2-(3-bromo-5-fluorobenzyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

Product 1

HCID 90280217(S)-methyl 2-amino-3-(3-bromo-5-fluorophenyl)propanoate hydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of (2S,5R)-2-(3-bromo-5-fluorobenzyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine (1.21 g, 3.27 mmol) in acetonitrile (15 mL) was treated with 0.3 N aqueous HCl (15 mL). The reaction was stirred for 2 h and then neutralized with the addition of 1N aq. NaOH. The acetonitrile was removed in vacuo and the solution was extracted with EtOAc. The organics were combined, dried over sodium sulfate, and removed in vacuo to provide (S)-methyl 2-amino-3-(3-bromo-5-fluorophenyl)propanoate hydrochloride (720 mg, 70%). MS (m/z) 276 [M+H]+.

Workup

  1. customThe acetonitrile was removed in vacuo
  2. extractionthe solution was extracted with EtOAc
  3. dry with materialdried over sodium sulfate
  4. customremoved in vacuo

Sources & evidence

ORD record
ord-b8b17199c0d342caa0078262c56130b9
Source dataset
uspto-grants-2015_04
Patent number
US09012441B2

Reaction notes

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