Trifluoroacetic acid → HCID 66865332, compound

HRID 1192911Notes

Reaction equation

HRID 1192911 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C:6]1([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:23][CH:22]=2)=[O:19])[CH2:9][N:8](C(OCCCC)=O)[CH2:7]1)[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:27]([C:24]1[CH:23]=[CH:22][C:21]([NH:20][C:18](=[O:19])[NH:17][C:6]2([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:35])[CH2:9][NH:8][CH2:7]2)=[CH:26][CH:25]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 86649847HCID 86649847, compound

Product 1

HCID 66865332HCID 66865332, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tent-butyl 3-(2-ethoxy-2-oxoethyl)-3-(3-(4-octylphenyl)ureido)azetidine-1-carboxylate (0.5 mmol) in CH2Cl2 (5 mL) was cooled with an ice/water bath and treated with trifluoroacetic acid (0.5 mL). The reaction was monitored (TLC) to completion (3-4 hrs) at which point the solvent and excess trifluoroacetic acid were removed in vacuo. The residue was purified by column chromatography to obtained the title compound (49 mg, 65%). 1H NMR (400 MHz, CD3OD) δ 7.21 (d, 2H, J=8.4 Hz), 7.07 (d, 2H, J=8.4 Hz), 4.14 (q, 2H, J=6.8 Hz), 3.80 (d, 2H, J=9.6 Hz), 3.69 (d, 2H, J=9.6 Hz), 3.11 (s, 2H), 2.55 (t, 2H, J=7.6 Hz), 1.60-1.55 (m, 2H), 1.33-1.21 (m, 13H), 0.90 (t, 3H, J=6.4 Hz); MS ESI 390.3 [M+H]+, calcd for [C22H35N3O3+H]+ 390.54.

Workup

  1. customto completion (3-4 hrs)
  2. customwere removed in vacuo
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ef5013bab60d41ceba4aad4e2915a860
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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