Carbon Dioxide → HCID 131712811, compound

HRID 2296551Notes

Reaction equation

HRID 2296551 reaction equation
[OH:1][CH:2]1[C@@H:6]2[CH2:7][C:8](=[O:9])[N:5]2[C:4]([C:10]([O:12][CH2:13][O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[O:11])=[C:3]1[CH3:21].[C:22](OC(=O)C)(=[O:24])[CH3:23].N1C=CC=CC=1.C(=O)=O>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.C(Cl)(Cl)Cl.C(Cl)Cl>[C:22]([O:1][CH:2]1[C@@H:6]2[CH2:7][C:8](=[O:9])[N:5]2[C:4]([C:10]([O:12][CH2:13][O:14][C:15](=[O:20])[C:16]([CH3:17])([CH3:19])[CH3:18])=[O:11])=[C:3]1[CH3:21])(=[O:24])[CH3:23]

Participants

9

Reactant 4

HCID 280Carbon DioxideHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 131712810HCID 131712810, compound

Product 1

HCID 131712811HCID 131712811, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the freshly prepared methylene chloride solution of pivaloyloxymethyl 1-hydroxy-2-methylcarbapen-2-em-3-carboxylate of Example 4, cooled to -78° C. was added acetic anhydride (0.170 ml., 1.68 mmoles), pyridine (0.144 ml., 1.68 mmoles) and 4-dimethylaminopyridine (10.5 mg., 0.086 mmoles) in two aliquots over 2 hours. The reaction was monitored by tlc (3:1 chloroform:ethyl acetate). After maintaining the reaction mixture at dry ice temperature for approximately 16 hours, additional 4-dimethylaminopyridine (0.5 mg.) was added and reaction continued for 2 hours at -78° C. The reaction mixture was extracted twice with aqueous buffer (pH 7), dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was chromatographed on 8 g. of silica gel (6:1 chloroform:ethyl acetate as eluant, monitored by tlc or ir spectral analysis) to yield pivaloyloxymethyl 1-acetoxy-2-methylcarbapen-2-em-3-carboxylate [15 mg,; ir (CH2Cl2) 1780, 1740 cm-1 ; Rf 0.75 (3:1 chloroform:ethyl acetate)].

Workup

  1. customreaction
  2. extractionThe reaction mixture was extracted twice with aqueous buffer (pH 7)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on 8 g

Sources & evidence

ORD record
ord-cd9f55cf060e456982058b2a10a9ea31
Source dataset
uspto-grants-1984_01
Patent number
US04429128

Reaction notes

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