Morpholine → HCID 131722178, compound

HRID 1858524Notes

Reaction equation

HRID 1858524 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:43](=[O:44])[N:13]3[C:14]([C:27]([O:29][CH:30]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[S:28])=[C:15]([C:18]4[S:19][CH:20]=[C:21]([CH2:23][C:24]([OH:26])=O)[N:22]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.[NH:67]1[CH2:72][CH2:71][O:70][CH2:69][CH2:68]1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:43](=[O:44])[N:13]3[C:14]([C:27]([O:29][CH:30]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[S:28])=[C:15]([C:18]4[S:19][CH:20]=[C:21]([CH2:23][C:24]([N:67]5[CH2:72][CH2:71][O:70][CH2:69][CH2:68]5)=[O:26])[N:22]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 5

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131722163HCID 131722163, compound

Product 1

HCID 131722178HCID 131722178, compoundYield 26.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzhydryl 7β-(2-phenylacetamido)-3-(4-carboxymethylthiazol-2-yl)thio-3-cephem-4-carboxylate (500 mg) in N,N-dimethylformamide (10 ml) were added 1-hydroxybenzotriazole (123 mg), WSC.HCl (175 mg) and morpholine (79 mg) at room temperature. After stirring at room temperature for 2.5 hours, the solution was poured into a mixture of water and ethyl acetate, and adjusted to pH 7.0 with aqueous sodium hydrogen carbonate. The separated organic layer was washed with saturated sodium chloride solution (×3), dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (eluent: ethyl acetate/n-hexane) to give benzhydryl 7β-(2-phenylacetamido)-3-(4-morpholinocarbonylmethylthiazol-2-yl)thio-3-cephem-4-carboxylate (147 mg).

Workup

  1. washThe separated organic layer was washed with saturated sodium chloride solution (×3)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-05ae2b34b662431e9cd7bdf3b79d4ce5
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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