Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 57308363 | HCID 57308363 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 21830457 | HCID 21830457 | — |
Reaction Steps
A solution of methyl (±)-7-[[[(2-benzimidazolyl)methyl]methylamino]carbonyl]-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (0.040 g, 0.09 mmol) in a mixture of methanol (7.0 mL), water (0.7 mL), and 1.0 M NaOH (0.7 mL) was kept 16 h at RT. Trifluoroacetic acid (0.5 mL) was added and the solvents were removed to give the crude product. Purification by semi-preparative HPLC (YMC ODS-AQ, 15:85; acetonitrile:water, 0.1% TFA) gave the title compound: MS (ES) m/e 408.2 (M+H)+ ; 1H NMR (250 MHz, DMSO-d6) δ 8.19 (br t, J=4.5 Hz, 1H), 7.72 (m, 2H), 7.38 (m, 2H), 7.28 (d, J=8.4 Hz, 1H), 7.15 (s, 1H), 6.62 (d, J=8.4 Hz, 1H), 6.22 (br s, 1H), 5.05 (m, 1H), 4.95 (s, 2H), 3.74 (dd, 15.8, 7.4 Hz, 1H), 3.15 (s, 3H), 2.75 (dd, J=16.4, 8.5 Hz, 1H), 2.50 (m, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05977101 |
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| Source dataset | uspto-grants-1999_11 |
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| ORD ID | ord-0b837385634c497082dca0efbdca05b2 |
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| Source note | uspto-grants-1999_11 |
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