Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | DL-cysteine | HCID 594 | — |
| Reactant | HCID 86654872 | HCID 86654872 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | HCID 58329597 | HCID 58329597 | 13.7% |
Reaction Steps
tert-Butyl 2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-ethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (6.6 mg, 0.012 mmol) was added to a solution of 2-amino-3-mercaptopropanoic acid (1.476 mg, 0.012 mmol) in TFA (1 mL). The reaction was stirred at 23° C. for 15 min in a 20 mL sealed scintillation vial. The mixture was poured into about 4 mL of ice water. The precipitate was collected by vacuum filtration through a glass fiber paper, washed with n-hexane (3×5 mL), and dried (vacuum oven) to give the title compound (0.8 mg) as a tan solid. LCMS m/z=486.3 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.09 (t, J=7.52 Hz, 3H), 1.48-1.59 (m, 2H), 1.60-1.69 (m, 2H), 1.74-1.82 (m, 2H), 1.93-2.00 (m, 2H), 2.17-2.27 (m, 1H), 2.39-2.49 (m, 1H), 2.55-2.63 (m, 2H), 2.66-2.81 (m, 2H), 3.21-3.32 (m, 1H), 3.54-3.63 (m, 1H), 3.82-3.89 (m, 1H), 3.92-4.00 (m, 1H), 5.05 (s, 2H), 6.70 (dd, J=8.72, 2.40 Hz, 1H), 6.96 (d, J=2.27 Hz, 1H), 7.03 (d, J=8.72 Hz, 1H), 7.49 (d, 1H), 7.57 (d, J=9.35 Hz, 1H), 7.64 (d, J=1.14 Hz, 1H), 8.95 (bs, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08415484B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-9025e38b130b4d5c92100bc82e3831dd |
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| Source note | uspto-grants-2013_04 |
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