Trifluoroacetic acid → HCID 67438014, compound

HRID 348121Notes

Reaction equation

HRID 348121 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:8]=2[CH2:9][NH:10]C(=O)OC(C)(C)C)=[O:6])[CH2:3][CH2:2]1.[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26]>C(Cl)Cl>[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26].[NH2:10][CH2:9][C:8]1[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:7]=1[C:5]([NH:4][CH:1]1[CH2:3][CH2:2]1)=[O:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67439676HCID 67439676, compound

Product 1

HCID 67438014HCID 67438014, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-(cyclopropylcarbamoyl)-4-fluorobenzylcarbamate (130 mg, 0.42 mmol) prepared according to literature methods, in CH2Cl2 (5 mL) was stirred with trifluoroacetic acid (3 mL) at room temperature for 10 min, then concentrated in vacuo to give 140 mg (Yield 100%) of the title compound as a foam: 1H NMR (DMSO-d6, 300 MHz) δ ppm: 0.62 (2H, m, CH2), 0.73 (2H, m, CH2), 2.86 (1H, m, CH), 4.02–4.07 (2H, ABq, NCH2), 7.46 (2H, m, Ar-Hs), 7.58 (1H, m, Ar—H), 8.11 (3H, br, NH3), 8.81 (1H, d, J=4.4 Hz, NH); LC/MS m/z 209 (M+H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-582bcbb625c2472aaae6ef85359e1851
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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