Trifluoroacetic acid → HCID 59180064, compound

HRID 601827Notes

Reaction equation

HRID 601827 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][CH:7]1[C:14]2[CH:13]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[N:11](C(OC(C)(C)C)=O)[C:10]=2[CH2:9][CH2:8]1)#[CH:2].FC(F)(F)C(O)=[O:32]>>[C:1]([C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][CH:7]1[C:14]2[CH:13]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[NH:11][C:10]=2[CH2:9][CH2:8]1)(=[O:32])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86638797HCID 86638797, compound2×

Product 1

HCID 59180064HCID 59180064, compound

Procedure

The title compound was synthesized from 1-tert-butyl 2-methyl 4-(3-ethynylbenzyl)-5,6-dihydrocyclopenta[b]pyrrole-1,2(4H)-dicarboxylate (see Example 2.51). 1-tert-Butyl 2-methyl 4-(3-ethynylbenzyl)-5,6-dihydrocyclopenta[b]pyrrole-1,2(4H)-dicarboxylate (0.016 g, 0.042 mmol) was dissolved in trifluoroacetic acid (1 mL) and stirred for 2 h. The reaction was then quenched with bicarbonate solution and extracted three times with ethyl acetate. The organic layer was dried over Na2SO4, concentrated and purified by column chromatography (Isco CombiFlash) eluting with a gradient of 0-25% EtOAc/heptane to afford the title compound. 0.006 g. 1H NMR (400 MHz, ACETONE-d6) δ ppm 2.07-2.16 (m, 1H) 2.49-2.55 (m, 1H) 2.57 (s, 3H) 2.61-2.68 (m, 2H) 2.88 (d, J=7.40 Hz, 2H) 3.29-3.37 (m, 1H) 3.70 (s, 3H) 6.28 (d, J=1.59 Hz, 1H) 7.41-7.50 (m, 2H) 7.82-7.87 (m, 2H) 10.48 (br. s, 1H).

Workup

  1. customThe reaction was then quenched with bicarbonate solution
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by column chromatography (Isco CombiFlash)
  6. washeluting with a gradient of 0-25% EtOAc/heptane

Sources & evidence

ORD record
ord-02af4c44528745f5add476c98637b8a2
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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