Morpholine → HCID 141573542, compound

HRID 1729565Notes

Reaction equation

HRID 1729565 reaction equation
[O:1]1[CH2:5][CH:4]([CH2:6]O)[O:3][CH2:2]1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[C:23]([NH:42][C:43]1[S:44][CH:45]=[C:46](/[C:48](=[N:80]/[O:81][C:82]([C:95]2[CH:100]=[CH:99][CH:98]=[CH:97][CH:96]=2)([C:89]2[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=2)[C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)/[C:49]([NH:51][CH:52]2[C:78](=[O:79])[N:54]3[C:55]([C:62]([O:64][CH:65]([C:72]4[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=4)[C:66]4[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=4)=[S:63])=[C:56](C(=O)C)[CH2:57][S:58][C@H:53]23)=[O:50])[N:47]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.N1CCOCC1.[F:107][C:108]([F:120])([F:119])[S:109]([O:112][CH2:113][CH:114]1[CH2:118][O:117][CH2:116][O:115]1)(=[O:111])=[O:110]>C(N(CC)CC)C.N1C=CC=CC=1>[F:120][C:108]([F:107])([F:119])[S:109]([O:112][CH2:113][CH:114]1[CH2:118][O:117][CH2:116][O:115]1)(=[O:111])=[O:110].[C:23]([NH:42][C:43]1[S:44][CH:45]=[C:46](/[C:48](=[N:80]/[O:81][C:82]([C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)([C:95]2[CH:96]=[CH:97][CH:98]=[CH:99][CH:100]=2)[C:89]2[CH:90]=[CH:91][CH:92]=[CH:93][CH:94]=2)/[C:49]([NH:51][CH:52]2[C:78](=[O:79])[N:54]3[C:55]([C:62]([O:64][CH:65]([C:66]4[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=4)[C:72]4[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=4)=[S:63])=[C:56]([CH2:6][CH:4]4[CH2:5][O:1][CH2:2][O:3]4)[CH2:57][S:58][C@H:53]23)=[O:50])[N:47]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

9

Reactant 5

HCID 8083MorpholineHCID 216181,3-Dioxolane-4-methanolHCID 67749Trifluoromethanesulfonic anhydrideHCID 19011599HCID 19011599, compoundHCID 141559367O-benzhydryl (6R)-3-acetyl-8-oxo-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbothioate

Product 2

HCID 19011599HCID 19011599, compoundHCID 141573542HCID 141573542, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

1,3-Dioxolan-4-ylmethyl trifluoromethanesulfonate was prepared in the same manner as in Example 27(a) from 1,3-dioxolan-4-yl-methanol (200 mg), pyridine (0.17 ml) and trifluoromethanesulfonic acid anhydride (596 mg). On the other hand, diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-acetylthio-3-cephem-4-carboxylate (700 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-dioxolan-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 (728 mg; 100%).

Workup

  1. customThe reaction solution so obtained
  2. additionwas post-treated in the same manner as in Example 27(b)
  3. customthe produced compound was recovered
  4. custompurified similarly to Example 27(b)

Sources & evidence

ORD record
ord-37f931d8652b4c72831ce0a6ec92c53e
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

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