Dicyclohexylcarbodiimide → HCID 131711649, compound
Reaction equation
[C:1]1([S:7]([CH2:9][C:10]([OH:12])=O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:28][CH:29]1[C:47](=[O:48])[N:31]2[C:32]([C:44]([OH:46])=[O:45])=[C:33]([CH2:36][S:37][C:38]3[S:42][C:41]([CH3:43])=[N:40][N:39]=3)[CH2:34][S:35][C@H:30]12>C(Cl)Cl.C(N(CC)CC)C.C(O)C>[C:1]1([S:7]([CH2:9][C:10]([NH:28][CH:29]2[C:47](=[O:48])[N:31]3[C:32]([C:44]([OH:46])=[O:45])=[C:33]([CH2:36][S:37][C:38]4[S:42][C:41]([CH3:43])=[N:40][N:39]=4)[CH2:34][S:35][C@H:30]23)=[O:12])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To 8 ml of methylene chloride were added 0.37 g of phenylsulfinylacetic acid of the R form ([α]D20 :+183°, C=1.00, ethanol) and 0.41 g of dicyclohexylcarbodiimide, and the mixture was agitated at room temperature for 1.5 hours. Then, a solution consisting of 0.69 g of 7-amino-3-(2-methyl-1,3,4-thiadiazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid, 0.28 ml of triethylamine and 8 ml of methylene chloride was added to the above mixture, and the resulting mixture was agitated at room temperature overnight. The reaction mixture was filtered, and the filtrate was post-treated in the same manner as described in Example 19 to obtain 0.17 g of 7-(phenylsulfinylacetamido)-3-(2-methyl-1,3,4-thiadiazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid of the R form, the IR and NMR spectra of which were found to be in agreement with those of the intended product.
Workup
- additionwas added to the above mixture
- stirringthe resulting mixture was agitated at room temperature overnight
- filtrationThe reaction mixture was filtered
- additionthe filtrate was post-treated in the same manner
Sources & evidence
- ORD record
- ord-424780152e7044458047f08477dc3e70
- Source dataset
- uspto-grants-1979_10
- Patent number
- US04172197
Reaction notes
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