Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | N-Methyl-D-glucamine | HCID 8567 | — |
| Reactant | Cyclohexanecarboxaldehyde | HCID 16275 | — |
| Reactant | {bicyclo[2.2.2]octan-1-yl}methanol | HCID 13245694 | — |
| Reactant | Benzyl 3-aminobenzoate | HCID 15428374 | — |
| Reactant | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Reactant | Benzyl 3-amino-2-methylbenzoate | HCID 54141052 | — |
| Reactant | HCID 178418287 | HCID 178418287 | — |
| Product | HCID 18405454 | HCID 18405454 | — |
Reaction Steps
The title compound was prepared according to the procedure of Example 216, with the modification that bicyclo[2.2.2]oct-1-yl-carbaldehyde (prepared by pyridinium chlorochromate oxidation of bicyclo[2.2.2]oct-1-yl-methanol (C. A. Grob, M. Ohta, E. Renk and A. Weiss, Helv. Chim. Acta 1958, 41, 1191)) was used in step d instead of cyclohexanecarboxaldehyde and 3-amino-2-methyl-benzoic acid benzyl ester replaced 3-amino-benzoic acid benzyl ester in step f. 1H NMR (300 MHz, d6-DMSO) 12.90 (1H, br s), 12.11 (1H, br s), 9.38 (1H, s), 8.01 (1H, d), 7.51 (1H, d), 7.28 (1H, t), 4.76 (2H, s), 2.40 (3H, s), 2.09 (3H, br s), 1.85-1.73 (12H, m), 1.64-1.52 (13H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.74; H, 7.99; N, 7.18%. C38H56N4O9.2.0 mols H2O requires: C, 60.94; H, 8.08; N, 7.48%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06479531B1 |
|---|
| Source dataset | uspto-grants-2002_11 |
|---|
| ORD ID | ord-e45fac9a981d49ab857b1f53f2f49d46 |
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| Source note | uspto-grants-2002_11 |
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