4-Methylmorpholine → HCID 131717474, compound

HRID 655056

Reaction equation

HRID 655056 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19]C(=O)CC4C=CC=CC=4)[C@H:15]3[S:14][CH2:13][C:12]=2[CH2:30][Cl:31])=[O:10])=[CH:5][CH:4]=1.CN1[CH2:40][CH2:39]OCC1.[C:41]([O:45][C:46]([NH:48][C:49]1[S:50][CH:51]=[C:52]([C:54](=[N:58][O:59][CH2:60][C:61](OC(C)(C)C)=O)[C:55]([OH:57])=O)[N:53]=1)=[O:47])([CH3:44])([CH3:43])[CH3:42].[CH:68]1[CH:73]=[CH:72][C:71](OP(Cl)(Cl)=O)=[CH:70][CH:69]=1>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([C:11]2[N:16]3[C:17](=[O:29])[C@@H:18]([NH:19][C:55](=[O:57])[C:54]([C:52]4[N:53]=[C:49]([NH:48][C:46]([O:45][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:47])[S:50][CH:51]=4)=[N:58][O:59][C:60]([C:61]4[CH:40]=[CH:39][CH:12]=[CH:11][CH:9]=4)([C:3]4[CH:33]=[CH:32][CH:6]=[CH:5][CH:4]=4)[C:68]4[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=4)[C@H:15]3[S:14][CH2:13][C:12]=2[CH2:30][Cl:31])=[O:10])=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 79724-Methylmorpholine2×HCID 13038Phosphorodichloridic acid, phenyl esterHCID 10874591(4-Methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-((2-phenylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylateHCID 537168652-(2-t-Butoxycarbonylamino-4-thiazolyl)-2-t-butoxycarbonylmethoxyiminoacetic acid

Product 1

HCID 131717474HCID 131717474, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-40 °C

Procedure

To a suspension of 7β-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (1) toluene-p-sulfonic acid salt (3.94 g; (7.28 mMol.) in dichloromethane (50 ml) keeping at 0° C. are added N-methylmorpholin (0.80 ml; 1 Eq.) and 2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-t-butoxycarbonylmethoxyiminoacetic acid (3.80 g; 1.3 Eq.) and cooled at -40° C. To this mixture are added phenylphosphoric acid dichloride (1.41 ml; 1.3 Eq.) and N-methylmorpholin (2.41 ml; 3 Eq.), and the mixture is stirred at -40° to -15° C. for 1.5 hours. The reaction mixture is diluted with ethyl acetate, washed with water, diluted hydrochloric acid and water, dried, and concentrated under reduced pressure. The residue is purified by silica gel chromatography (toluene toluene: ethyl acetate) to give 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-t-butoxycarbonylmethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (2) (5.20 g).

Workup

  1. customkeeping at 0° C.
  2. washwashed with water, diluted hydrochloric acid and water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel chromatography (toluene toluene: ethyl acetate)

Sources & evidence

ORD record
ord-871313f628f1425fba0d1c59af88520e
Source dataset
uspto-grants-1992_07
Patent number
US05134138

Linked notes

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