4-Methylmorpholine → HCID 178452987, compound

HRID 249608Notes

Reaction equation

HRID 249608 reaction equation
Cl.[C:2]1([CH:8]([O:15][C:16]([C:18]2[N:23]3[C:24](=[O:27])[C@@H:25]([NH2:26])[C@H:22]3[S:21][CH2:20][C:19]=2[CH2:28][S:29][C:30]2[N:31]=[N:32][NH:33][CH:34]=2)=[S:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([O:39][C:40]([NH:42][C:43]1[S:44][CH:45]=[C:46](/[C:48](=[N:52]/[O:53][C:54]([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)/[C:49](O)=[O:50])[N:47]=1)=[O:41])([CH3:38])([CH3:37])[CH3:36].CN1CCOCC1.P(Cl)(Cl)(OC1C=CC=CC=1)=O>ClCCl.Cl>[C:2]1([CH:8]([O:15][C:16]([C:18]2[N:23]3[C:24](=[O:27])[C@@H:25]([NH:26][C:49](=[O:50])/[C:48](/[C:46]4[N:47]=[C:43]([NH:42][C:40]([O:39][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:41])[S:44][CH:45]=4)=[N:52]\[O:53][C:54]([C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)[C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)[C@H:22]3[S:21][CH2:20][C:19]=2[CH2:28][S:29][C:30]2[N:31]=[N:32][NH:33][CH:34]=2)=[S:17])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 13038Phosphorodichloridic acid, phenyl esterHCID 10459636(Z)-2-(2-Boc-aminothiazole-4-yl-)-2-trityloxyiminoacetic acidHCID 178479291HCID 178479291, compound

Product 1

HCID 178452987HCID 178452987, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 7β-amino-3-(1,2,3-triazol-4-yl) thiomethylthio- 3-cephem-4-carboxylic acid diphenylmethyl ester hydrochloride (110 mg: 0.2 mMol.) and (Z)-2-(2-t-butoxycarbonylaminothiazol -4-yl)-2-trityloxyiminoacetic acid (122 mg: 0.23 mMol.) in dichloromethane (3 ml) are added N-methylmorpholine (72 μl: 0.66 mMol.) and phenyl dichlorophosphate (33 μl : 0.22 mMol.) at -30° C. After stirring for 2 hours, the reaction mixture is diluted with 10% hydrochloric acid and extracted with ethyl acetate. The extract is washed with water dried, purified by silica gel chromatography, and crystallized from toluene to give 7β- [(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]- 3-(1,2,3-triazol-4-yl) thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (110 mg). m.p. 190°-200° C. (decomp.).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water
  3. customdried
  4. custompurified by silica gel chromatography
  5. customcrystallized from toluene

Sources & evidence

ORD record
ord-51e70c6329d54158b7547995391497d4
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

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