Trifluoroacetic acid → (S)-2-amino-1-(5-ethyl-1,2,4-oxadiazol-3-yl)-butan-1-ol trifluoroacetate

HRID 1765682Notes

Reaction equation

HRID 1765682 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH:11]([C:13]1[N:17]=[C:16]([CH2:18][CH3:19])[O:15][N:14]=1)[OH:12])[CH2:9][CH3:10])(C)(C)C.[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24]>C(Cl)Cl>[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24].[NH2:7][CH:8]([CH2:9][CH3:10])[C@@H:11]([C:13]1[N:17]=[C:16]([CH2:18][CH3:19])[O:15][N:14]=1)[OH:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69426245{(S)-1-[(5-ethyl-1,2,4-oxadiazol-3-yl)-hydroxy-methyl]-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 69427127(S)-2-amino-1-(5-ethyl-1,2,4-oxadiazol-3-yl)-butan-1-ol trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {(S)-1-[(5-ethyl-1,2,4-oxadiazol-3-yl)-hydroxy-methyl]-propyl}-carbamic acid tert-butyl ester (214 mg, 0.751 mmol) in methylene chloride (5 mL) was treated with trifluoroacetic acid (0.578 mL, 7.504 mmol) and stirred at room temperature for 3 hours. Solvent evaporated under reduced pressure to give (S)-2-amino-1-(5-ethyl-1,2,4-oxadiazol-3-yl)-butan-1-ol trifluoroacetate, a mixture of diastereoisomers, (224 mg) as a brown oil.

Workup

  1. customSolvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-09db3a55038e413d81c0170ae50a8c0e
Source dataset
uspto-grants-2007_06
Patent number
US07226921B2

Reaction notes

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