Water → 1-Isopropoxycarbonyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

HRID 1632763Notes

Reaction equation

HRID 1632763 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([O-:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].I[CH:28]([O:30][C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[CH3:29].O.C(OCC)(=O)C>CS(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([O:20][CH:28]([O:30][C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[CH3:29])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 110106451-Iodoethyl isopropyl carbonateHCID 131712445Sodium 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

Product 1

HCID 1317139301-Isopropoxycarbonyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylateYield 29.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer) (4.0 g) in dimethylsulfoxide (40 ml) was added isopropyl 1-iodoethoxyformate (5.1 g). The mixture was stirred for 30 minutes at ambient temperature and poured into a mixture of cold water and ethyl acetate. The organic layer was separated out and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water, dried over magnesium sulfate and evaporated to dryness. The residue was subjected to column chromatography on silica gel (50 g) using a mixture of benzene and ethyl acetate (3:2) as an eluent. The eluates containing an object compound were collected and evaporated to dryness to give 1-isopropoxycarbonyloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer) (1.5 g), mp 120° to 125° C. (dec.).

Workup

  1. customThe organic layer was separated out
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. additiona mixture of benzene and ethyl acetate (3:2) as an eluent
  7. additionThe eluates containing an object compound
  8. customwere collected
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-61fae8b743944ede9c1f023012b0ed7b
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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