Trifluoroacetic acid → HCID 86722574, compound

HRID 1503788Notes

Reaction equation

HRID 1503788 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][NH:4][C:5]([C:7]1([NH:11]C(=O)OC(C)(C)C)[CH2:10][CH2:9][CH2:8]1)=[O:6].[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]([O-:25])=[O:24].[F:1][C:2]([F:19])([F:20])[CH2:3][NH:4][C:5]([C:7]1([NH3+:11])[CH2:10][CH2:9][CH2:8]1)=[O:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86722575HCID 86722575, compound

Product 1

HCID 86722574HCID 86722574, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 1-(2,2,2-trifluoroethylcarbamoyl)cyclobutylcarbamate (500 mg, 1.68 mmol) in CH2Cl2 (10 mL) was added trifluoroacetic acid (TFA, 1.0 mL) dropwise and the reaction mixture was stirred overnight. The volatiles were evaporated and the residue was triturated with pentane to give the title compound as colorless gum which was taken on to the next step without further purification (400 mg, 77%): 1H NMR (300 MHz, DMSO-d6) δ 9.14 (t, J=6.0 Hz, 1H), 8.52 (bs, 2H), 4.08-3.96 (m, 2H), 2.63-2.55 (m, 2H), 2.27-2.14 (m, 2H), 2.08-2.00 (m, 2H); ESIMS m/z 196.9 ([M+H]+); IR (thin film) 3364, 2949, 1680, 1033 cm−1.

Workup

  1. customThe volatiles were evaporated
  2. customthe residue was triturated with pentane

Sources & evidence

ORD record
ord-c9efdabbf4cf4ad0b89f7c512d9f2701
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

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