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

HRID 1729564Notes

Reaction equation

HRID 1729564 reaction equation
[O:1]1[CH2:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3][CH2:2]1.[C:9]([NH:28][C:29]1[S:30][CH:31]=[C:32](/[C:34](=[N:66]/[O:67][CH3:68])/[C:35]([NH:37][CH:38]2[C:64](=[O:65])[N:40]3[C:41]([C:48]([O:50][CH:51]([C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=4)[C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)=[S:49])=[C:42]([C:45](=O)C)[CH2:43][S:44][C@H:39]23)=[O:36])[N:33]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1CCOCC1.[F:75][C:76]([F:89])([F:88])[S:77](OC[CH:82]1[CH2:87][CH2:86][O:85][CH2:84][O:83]1)(=[O:79])=[O:78]>FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(N(CC)CC)C.N1C=CC=CC=1>[F:75][C:76]([F:89])([F:88])[S:77]([O:8][CH2:7][CH:5]1[CH2:4][O:3][CH2:2][O:1][CH2:6]1)(=[O:79])=[O:78].[C:9]([NH:28][C:29]1[S:30][CH:31]=[C:32](/[C:34](=[N:66]/[O:67][CH3:68])/[C:35]([NH:37][CH:38]2[C:64](=[O:65])[N:40]3[C:41]([C:48]([O:50][CH:51]([C:58]4[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=4)[C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)=[S:49])=[C:42]([CH2:45][CH:87]4[CH2:82][O:83][CH2:84][O:85][CH2:86]4)[CH2:43][S:44][C@H:39]23)=[O:36])[N:33]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

9

Reactant 4

HCID 8083MorpholineHCID 2839921,3-dioxan-5-ylmethanolHCID 19011617HCID 19011617, compoundHCID 139642673O-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

Product 2

HCID 190115751,3-Dioxan-5-ylmethyl trifluoromethanesulfonateHCID 141573527O-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-carbothioateYield 92%

Reagents, catalysts & solvents 3

HCID 67749Trifluoromethanesulfonic anhydrideCatalystHCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

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%).

Workup

  1. customThe reaction solution so obtained
  2. customthe produced compound was recovered

Sources & evidence

ORD record
ord-5ad0ad7836ea4a02a6b3368e16e99bd9
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

Loading…