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1,4-Dioxane hydrochloride → (S)-ethyl 2-amino-4-fluoro-3,3-dimethylbutanoate HCl

HRID 520361
Notes
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Reaction equation

HRID 520361 reaction equation
CC(C)([S@@]([NH:6][C@@H:7]([C:13]([CH3:17])([CH3:16])[CH2:14][F:15])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=O)C.[ClH:19].O1CCOCC1>CO>[NH2:6][C@@H:7]([C:13]([CH3:16])([CH3:17])[CH2:14][F:15])[C:8]([O:10][CH2:11][CH3:12])=[O:9].[ClH:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86690080(S)-ethyl 2-((S)-1,1-dimethylethylsulfinamido)-4-fluoro-3,3-dimethylbutanoate

Product 1

HCID 86690081(S)-ethyl 2-amino-4-fluoro-3,3-dimethylbutanoate HClYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-ethyl 2-((S)-1,1-dimethylethylsulfinamido)-4-fluoro-3,3-dimethylbutanoate (0.38 g, 1.350 mmol) in MeOH (10 mL) was added HCl/dioxane (1.350 mL, 5.40 mmol). The reaction mixture was stirred at rt for 30 min and concentrated to afford (S)-ethyl 2-amino-4-fluoro-3,3-dimethylbutanoate/HCl as a white solid (0.29 g).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-dca3387010364996ab7fc060d28b598f
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09326973B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes