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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1729564Generated: October 31, 2026

Morpholine → O-benzhydryl (6R)-3-(1,3-dioxan-5-ylmethyl)-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

https://huagongshe.com/reaction/1729564

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMorpholineHCID 8083—
Reactant1,3-dioxan-5-ylmethanolHCID 283992—
ReactantHCID 19011617HCID 19011617—
ReactantO-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-carbothioateHCID 139642673—
CatalystTrifluoromethanesulfonic anhydrideHCID 67749—
SolventPyridineHCID 1049—
SolventTriethylamineHCID 8471—
Product1,3-Dioxan-5-ylmethyl trifluoromethanesulfonateHCID 19011575—
ProductO-benzhydryl (6R)-3-(1,3-dioxan-5-ylmethyl)-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-carbothioateHCID 14157352792%

Reaction Steps

1,3-Dioxan-5-ylmethyl trifluoromethanesulfonate was prepared in the same manner as in Example 27 (a) from 1,3-dioxan-5-ylmethanol (205 mg), pyridine (0.15 ml) and trifluoromethanesulfonic acid anhydride (5.39 mg). On the other hand, diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl) -2-methoxyiminoacetamido]-3-acetylthio-3-cephem-4-carboxylate (500 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 1,3-dioxan-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 (490 mg; 92%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05332731
Source datasetuspto-grants-1994_07
ORD IDord-5ad0ad7836ea4a02a6b3368e16e99bd9
Source noteuspto-grants-1994_07