Isobutanol → HCID 70457302, compound

HRID 2057603Notes

Reaction equation

HRID 2057603 reaction equation
[Cl:1][Cl:2].[P:3]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.C(O)C(C)C>C(Cl)Cl>[P:3]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1.[Cl:1][Cl:2]

Participants

6

Reactant 4

HCID 6560IsobutanolHCID 7540Triphenyl phosphite2×HCID 8471TriethylamineHCID 24526Chlorine2×

Product 1

HCID 70457302HCID 70457302, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of the triphenyl phosphite-chlorine kinetic complex was prepared by adding chlorine gas simultaneously with 3.16 ml (12 mmol) of triphenyl phosphite to 45 ml of methylene chloride at -10° C. A slight yellow color was maintained throughout the preparation. An additional 0.5 mmol of triphenyl phosphite was added to dissipate the yellow chlorine color. To the resulting solution was added 4.84 gm (10 mmol) of 4'-nitrobenzyl 7-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate which was washed into the mixture with 5 ml of methylene chloride. After 5 minutes 1.8 ml (13 mmol) of triethylamine in 8 ml of methylene chloride were added over a 15 minute period. After stirring the reaction mixture for 15 minutes at -10° C., the cooling bath was removed from the reaction mixture and 5.1 ml (55 mmol) of isobutanol was added. Thereafter HCl gas was bubbled into the reaction mixture for about 3 minutes. The reaction mixture was seeded and allowed to warm to room temperature. After 2 hours at room temperature the reaction mixture was filtered to provide 1.28 grams (33.2%) of the nucleus hydrochloride ester: m.p. 180.5° C. (dec.).

Workup

  1. temperatureA slight yellow color was maintained throughout the preparation
  2. washwas washed into the mixture with 5 ml of methylene chloride
  3. additionwas added
  4. customThereafter HCl gas was bubbled into the reaction mixture for about 3 minutes
  5. temperatureto warm to room temperature
  6. filtrationAfter 2 hours at room temperature the reaction mixture was filtered

Sources & evidence

ORD record
ord-02f041370b9c45c6998363eaea5b6e2f
Source dataset
uspto-grants-1980_07
Patent number
US04211702

Reaction notes

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