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Phosphorus pentachloride → 7-[2-Ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate

HRID 1163879
Notes
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Reaction equation

HRID 1163879 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:9]1[N:10]=[C:11]([NH:14][CH:15]=[O:16])[S:12][CH:13]=1)[C:6]([OH:8])=O)[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.C[Si](C)(C)NC(=O)C.O.O.Cl.[Cl-].[NH2:35][CH:36]1[C:53](=[O:54])[N:38]2[C:39]([C:50]([OH:52])=[O:51])=[C:40]([CH2:43][N+:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:41][S:42][C@H:37]12>ClCCl.O1CCCC1.C(OCC)(=O)C.O.C(N(CC)CC)C>[CH2:1]([O:3][N:4]=[C:5]([C:9]1[N:10]=[C:11]([NH:14][CH:15]=[O:16])[S:12][CH:13]=1)[C:6]([NH:35][CH:36]1[C:53](=[O:54])[N:38]2[C:39]([C:50]([O-:52])=[O:51])=[C:40]([CH2:43][N+:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH2:41][S:42][C@H:37]12)=[O:8])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 24819Phosphorus pentachlorideHCID 25989Acetamide, N-(trimethylsilyl)-HCID 544580772-(2-Formamidothiazol-4-yl)-2-ethoxyiminoacetic acidHCID 70450238HCID 70450238, compound

Product 1

HCID 1317129237-[2-Ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylateYield 39.3%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Ethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (2.2 g) was added to a solution of phosphorus pentachloride (2.0 g) in dichloromethane (40 ml) at -10° C., and stirred at -5° C. to -10° C. for 1 hour. After the addition of triethylamine (2.0 g), the resulting mixture was stirred at -5° C. for 5 minutes [Solution A]. N-trimethylsilylacetamide (9.8 g) was added to a stirred suspension of 1-[(7-amino-4-carboxy-3-cephem-3-yl)methyl]pyridinium chloride hydrochloride dihydrate (3.0 g) in dry tetrahydrofuran (60 ml), and the mixture was stirred for 20 minutes at 35° C. to 40° C. To the solution was added the solution A at -10° C. and the resulting solution was stirred at the same temperature for 40 minutes. Water and ethyl acetate were added to the reaction mixture at -10° C. and the separated aqueous layer was washed with ethyl acetate and adjusted to pH 4.0 with 10% aqueous solution of sodium hydroxide. The resulting solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: Prepared by Mitsubishi Chemical Industries) and eluted with 10% aqueous solution of isopropyl alcohol. The fractions containing the object compound were collected and concentrated and lyophilized to give 7-[2-ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.52 g).

Workup

  1. stirringthe mixture was stirred for 20 minutes at 35° C. to 40° C
  2. stirringthe resulting solution was stirred at the same temperature for 40 minutes
  3. washthe separated aqueous layer was washed with ethyl acetate
  4. customThe resulting solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: Prepared by Mitsubishi Chemical Industries)
  5. washeluted with 10% aqueous solution of isopropyl alcohol
  6. additionThe fractions containing the object compound
  7. customwere collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c95f5b576d244dff86f896a36031c7bf
Source dataset
uspto-grants-1983_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04367228

Reaction notes

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