Trifluoroacetic acid → HCID 67438014, compound

HRID 1726559Notes

Reaction equation

HRID 1726559 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-400661071218473c9f1e8f558f46f08b
Source dataset
uspto-grants-2009_02
Patent number
US07491819B1

Reaction notes

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