Morpholine → HCID 141573540, compound

HRID 1729567Notes

Reaction equation

HRID 1729567 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7]O)[CH2:3][CH2:2]1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[C:24]([NH:43][C:44]1[S:45][CH:46]=[C:47](/[C:49](=[N:81]/[O:82][C:83]([C:96]2[CH:101]=[CH:100][CH:99]=[CH:98][CH:97]=2)([C:90]2[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=2)[C:84]2[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=2)/[C:50]([NH:52][CH:53]2[C:79](=[O:80])[N:55]3[C:56]([C:63]([O:65][CH:66]([C:73]4[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=4)[C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)=[S:64])=[C:57](C(=O)C)[CH2:58][S:59][C@H:54]23)=[O:51])[N:48]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.N1CCOCC1.[F:108][C:109]([F:122])([F:121])[S:110]([O:113][CH2:114][CH:115]1[CH2:120][CH2:119][O:118][CH2:117][CH2:116]1)(=[O:112])=[O:111]>C(N(CC)CC)C.N1C=CC=CC=1>[F:121][C:109]([F:108])([F:122])[S:110]([O:113][CH2:114][CH:115]1[CH2:116][CH2:117][O:118][CH2:119][CH2:120]1)(=[O:111])=[O:112].[C:24]([NH:43][C:44]1[S:45][CH:46]=[C:47](/[C:49](=[N:81]/[O:82][C:83]([C:84]2[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=2)([C:96]2[CH:97]=[CH:98][CH:99]=[CH:100][CH:101]=2)[C:90]2[CH:91]=[CH:92][CH:93]=[CH:94][CH:95]=2)/[C:50]([NH:52][CH:53]2[C:79](=[O:80])[N:55]3[C:56]([C:63]([O:65][CH:66]([C:67]4[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=4)[C:73]4[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=4)=[S:64])=[C:57]([CH2:7][CH:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)[CH2:58][S:59][C@H:54]23)=[O:51])[N:48]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

9

Reactant 5

HCID 8083MorpholineHCID 67749Trifluoromethanesulfonic anhydrideHCID 2773573(Oxan-4-yl)methanolHCID 19011570Tetrahydropyran-4-ylmethyl trifluoromethanesulfonateHCID 141559367HCID 141559367, compound

Product 2

HCID 19011570Tetrahydropyran-4-ylmethyl trifluoromethanesulfonateHCID 141573540HCID 141573540, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

Tetrahydropyran-4-ylmethyl trifluoromethanesulfonate was prepared in the same manner as in Example 27 (a) from tetrahydropyran-4-yl-methanol (223 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 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 (722 mg; 98%).

Workup

  1. customso obtained
  2. customthe produced compound was recovered

Sources & evidence

ORD record
ord-b18fe417a76e4582b78d4bc27bceb4bd
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

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