Trifluoroacetic acid → 3-Azetidineacetic acid trifluoroacetate

HRID 1177418Notes

Reaction equation

HRID 1177418 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([CH2:12][C:13]([OH:15])=[O:14])[CH2:9]1)=O)(C)(C)C.[F:16][C:17]([F:22])([F:21])[C:18]([OH:20])=[O:19]>ClCCl>[F:16][C:17]([F:22])([F:21])[C:18]([OH:20])=[O:19].[NH:8]1[CH2:11][CH:10]([CH2:12][C:13]([OH:15])=[O:14])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 110959892-(1-(Tert-butoxycarbonyl)azetidin-3-yl)acetic acid

Product 1

HCID 671126063-Azetidineacetic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(1-(tert-Butoxycarbonyl)azetidin-3-yl)acetic acid (0.308 g, 1.43 mmol) was dissolved in 5 mL dichloromethane and was stirred at room temperature. Trifluoroacetic acid (1.47 mL) was added dropwise to the reaction mixture at 0° C. The reaction mixture was allowed to stir at room temperature for 2 h. Trifluoroacetic acid was removed in vacuo to give 2-(azetidin-3-yl)acetic acid trifluoroacetic acid salt. 1H-NMR (400 MHz, CDCl3) δ ppm 4.18-4.13 (m, 2H), 3.93-3.88 (m, 2H), 3.25-3.19 (m, 1H), 2.71 (d, 2H, J=7.6 Hz).

Workup

  1. stirringto stir at room temperature for 2 h
  2. customTrifluoroacetic acid was removed in vacuo

Sources & evidence

ORD record
ord-d1446ba87abe4b92a6a421a42345f77e
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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