Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Trifluoromethanesulfonic anhydride | HCID 67749 | — |
| Reactant | (Oxan-4-yl)methanol | HCID 2773573 | — |
| Reactant | Tetrahydropyran-4-ylmethyl trifluoromethanesulfonate | HCID 19011570 | — |
| Reactant | O-benzhydryl (6R)-3-acetyl-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbothioate | HCID 139642673 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | Tetrahydropyran-4-ylmethyl trifluoromethanesulfonate | HCID 19011570 | — |
| Product | HCID 141573524 | HCID 141573524 | 98% |
Reaction Steps
Tetrahydropyran-4-ylmethyl trifluoromethanesulfonate was prepared in the same manner as in Example 27(a) from tetrahydropyran-4-yl-methanol (348 mg), pyridine (0.27 ml) and trifluoromethanesulfonic acid anhydride (931 mg). On the other hand, diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido]-3-acetylthio-3-cephem-4-carboxylate (866 mg) was reacted with morpholine and triethylamine in the same manner as in Example 27(b), followed by reacting the resulting reaction product with the tetrahydropyran-4-ylmethyl trifluoromethanesulfonate in the same manner as in Example 27(b). The reaction solution so obtained was post-treated in the same manner as in Example 27(b) and the produced compound was recovered and purified similarly to Example 27 (b) to afford the titled compound (904 mg; 98%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05332731 |
|---|
| Source dataset | uspto-grants-1994_07 |
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| ORD ID | ord-9f19f6da194e41b19e41081da01a2942 |
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| Source note | uspto-grants-1994_07 |
|---|
