Diisopropyl Ether → HCID 131714207, compound

HRID 1906082Notes

Reaction equation

HRID 1906082 reaction equation
C([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:28]1[N:29]=[CH:30][S:31][CH:32]=1)[C:12]([NH:14][CH:15]1[C:26](=[O:27])[N:17]2[C:18]([C:23]([OH:25])=[O:24])=[C:19]([CH3:22])[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])(C)(C)C.C(OC(C)C)(C)C.CCCCCC>C(Cl)Cl.C1(OC)C=CC=CC=1>[C:6]([CH2:8][O:9][N:10]=[C:11]([C:28]1[N:29]=[CH:30][S:31][CH:32]=1)[C:12]([NH:14][CH:15]1[C:26](=[O:27])[N:17]2[C:18]([C:23]([OH:25])=[O:24])=[C:19]([CH3:22])[CH2:20][S:21][C@H:16]12)=[O:13])([OH:7])=[O:5]

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 8058HexaneHCID 131714208HCID 131714208, compound

Product 1

HCID 131714207HCID 131714207, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic aid (8.4 ml) was added to a suspension of 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-methyl-3-cephem-4-carboxylic acid (syn isomer) (2.1 g) in methylene chloride (4.2 ml) and anisole (2.1 ml) at ambient temperature and the mixture was stirred for 1.5 hours at the same temperature. To the resultant solution was added diisopropyl ether (50 ml) and n-hexane (30 ml) and the mixture was stirred. The precipitates were collected by filtration, washed with a solution of diisopropyl ether and n-hexane (1:1). The precipitates were added to a mixture of ethyl acetate and water, and the mixture was adjusted to pH 7.0 with saturated aqueous solution of potassium carbonate. The separated aqueous layer was adjusted to pH 4 with 10% hydrochloric acid and the solution was washed with ethyl acetate. The aqueous layer was adjusted to pH 1.8 with 10% hydrochloric acid and saturated with sodium chloride. The acidic solution was extracted with ethyl acetate and tetrahydrofuran (1:1). The extract was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 7-[2-carboxymethoxyimino-2-(4-thiazolyl)acetamido]-3-methyl-3-cephem-4-carboxylic acid (syn isomer) (1.0 g).

Workup

  1. stirringthe mixture was stirred
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with a solution of diisopropyl ether and n-hexane (1:1)
  4. additionThe precipitates were added to a mixture of ethyl acetate and water
  5. washthe solution was washed with ethyl acetate
  6. extractionThe acidic solution was extracted with ethyl acetate and tetrahydrofuran (1:1)
  7. washThe extract was washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-81fdb6e2755b4d159e35fb4aee088de6
Source dataset
uspto-grants-1987_03
Patent number
US04649136

Reaction notes

Loading…