Trifluoroacetic acid → Trifluoroacetic acid

HRID 2044088Notes

Reaction equation

HRID 2044088 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]1([C:14]2[CH2:18][C:17]3([CH2:23][CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]3)[O:16][N:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[C:8]1([C:14]2[CH2:18][C:17]3([CH2:23][CH2:22][CH2:21][NH:20][CH2:19]3)[O:16][N:15]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1.[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57489637tert-Butyl 3-phenyl-1-oxa-2,7-diazaspiro[4.5]dec-2-ene-7-carboxylate

Product 2

HCID 6422Trifluoroacetic acidYield 287.9%HCID 569344603-Phenyl-1-oxa-2,7-diazaspiro[4.5]dec-2-ene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL, 26.0 mmol) was added dropwise to a solution of tert-butyl 3-phenyl-1-oxa-2,7-diazaspiro[4.5]dec-2-ene-7-carboxylate (270 mg, 0.853 mmol) in CH2Cl2 (5 mL) at room temperature. After 1 h at room temperature, the mixture was concentrated to give the expected product as TFA salt (280 mg, 99% yield). LCMS: (M+H)+=217.15. 1H NMR (400 MHz, methanol-d4) δ ppm 7.62-7.78 (2H, m), 7.36-7.51 (3H, m), 3.35-3.49 (4H, m), 3.00-3.24 (2H, m), 2.04-2.22 (2H, m), 1.85-2.07 (2H, m).

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-f00afcc1b8a44b5ca663a70728b4bad2
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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