Hydrochloric Acid → HCID 131716197, compound

HRID 1638845Notes

Reaction equation

HRID 1638845 reaction equation
[CH:1]([O:14][C:15]([CH:17]([O:38][N:39]=[C:40]([C:44]1[N:45]=[C:46]([NH:49][C:50]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[S:47][CH:48]=1)[C:41](O)=[O:42])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])=[C:20]([O:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37])[CH:19]=1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:69][CH:70]1[C:95](=[O:96])[N:72]2[C:73]([C:79]([O:81][CH:82]([C:89]3[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=3)[C:83]3[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=3)=[O:80])=[C:74]([CH2:77][Cl:78])[CH2:75][S:76][C@H:71]12.CN(C)C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O.Cl>C(Cl)Cl>[CH:1]([O:14][C:15]([CH:17]([O:38][N:39]=[C:40]([C:44]1[N:45]=[C:46]([NH:49][C:50]([C:63]2[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[S:47][CH:48]=1)[C:41]([NH:69][CH:70]1[C:95](=[O:96])[N:72]2[C:73]([C:79]([O:81][CH:82]([C:83]3[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=3)[C:89]3[CH:90]=[CH:91][CH:92]=[CH:93][CH:94]=3)=[O:80])=[C:74]([CH2:77][Cl:78])[CH2:75][S:76][C@H:71]12)=[O:42])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])=[C:20]([O:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37])[CH:19]=1)=[O:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 13239626Benzhydryl 7-Amino-3-chloromethyl-3-cephem-4-carboxylateHCID 54043218HCID 54043218, compound

Product 1

HCID 131716197HCID 131716197, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.87 g (5.19 mmol) of 2-[α-benzhydryloxycarbonyl-3,4-di(2-methoxyethoxymethoxy)benzyloxyimino]-2-(tritylaminothiazol-4-yl)acetic acid (syn-isomer) and 2.34 g (5.64 mmol) of benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate were dissolved in 90 ml of methylene chloride, and 3.2 ml (25.4 mmol) of N,N-dimethylaniline and 0.63 ml (6.77 mmol) of phosphorus oxychloride were dropwise added at 0° C. The mixture was stirred for 1 hour. The reaction solution was poured into 1N hydrochloric acid, and extracted with 1N methylene chloride aqueous solution. The organic phase was washed with 1N sodium hydroxide aqueous solution and a saturated sodium chloride aqueous solution. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to obtain a crude benzhydryl 7-{2-[α-benzhydryloxycarbonyl-3,4-di(2-methoxyethoxymethoxy)benzyloxyimino]-2-(tritylaminothiazol-4-yl)acetamido}-3-chloromethyl-3-cephem-4-carboxylate (syn-isomer), which was used for the next reaction without purification.

Workup

  1. extractionextracted with 1N methylene chloride aqueous solution
  2. washThe organic phase was washed with 1N sodium hydroxide aqueous solution
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a0228268727c4cb4bf2e1d1448b5552c
Source dataset
uspto-grants-1989_11
Patent number
US04880797

Reaction notes

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