GB544051A - Improvements in the preparation of 3-acyloxy-bisnor-cholanic acids - Google Patents

Improvements in the preparation of 3-acyloxy-bisnor-cholanic acids

Info

Publication number
GB544051A
GB544051A GB1436840A GB1436840A GB544051A GB 544051 A GB544051 A GB 544051A GB 1436840 A GB1436840 A GB 1436840A GB 1436840 A GB1436840 A GB 1436840A GB 544051 A GB544051 A GB 544051A
Authority
GB
United Kingdom
Prior art keywords
acid
acyloxy
unsaturated
bisnorcholanic
prepared
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB1436840A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to GB1436840A priority Critical patent/GB544051A/en
Publication of GB544051A publication Critical patent/GB544051A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

544,051. 3-Acyloxy-bisnorcholanic acid. BERGMAN, E. Sept. 19, 1940, No. 14368. [Class 2 (iii)] 3-Acyloxy-bisnorcholanic acid is prepared from acyl lithocholic acid by forming the acid halide, brominating and treating the α-bromo acid thus produced with an acid binding agent to withdraw hydrobromic acid to form the corresponding α-#-unsaturated acid. This is then oxidized to form the required 3-acyloxybisnorcholanic acid. In an example lithocholic acid prepared by the chromic acid oxidation of the benzoyl derivative of methyl desoycholate is converted into acetyl derivative, treated with thionyl chloride to form the corresponding acid chloride, brominated with the theoretical amount of bromine in the presence of red phosphorus, and the bromine removed with pyridine to form the α-#-unsaturated acid. Chromic acid oxidation of this unsaturated acid in glacial acetic acid solution yields the required 3-acetyl-bisnorlithocholic acid.
GB1436840A 1940-09-19 1940-09-19 Improvements in the preparation of 3-acyloxy-bisnor-cholanic acids Expired GB544051A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1436840A GB544051A (en) 1940-09-19 1940-09-19 Improvements in the preparation of 3-acyloxy-bisnor-cholanic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1436840A GB544051A (en) 1940-09-19 1940-09-19 Improvements in the preparation of 3-acyloxy-bisnor-cholanic acids

Publications (1)

Publication Number Publication Date
GB544051A true GB544051A (en) 1942-03-25

Family

ID=10039951

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1436840A Expired GB544051A (en) 1940-09-19 1940-09-19 Improvements in the preparation of 3-acyloxy-bisnor-cholanic acids

Country Status (1)

Country Link
GB (1) GB544051A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2461910A (en) * 1942-08-18 1949-02-15 Ciba Pharm Prod Inc Process for the degradation of the side-chain of steroids and steroids suitable therefor
US2461911A (en) * 1946-08-01 1949-02-15 Ciba Pharm Prod Inc Process for the degradation of the side-chain of steroids and steroids suitable therefor
US2461912A (en) * 1942-08-18 1949-02-15 Ciba Pharm Prod Inc Process for the degradation of the side-chain of a steroid containing a nuclear alpha, beta-unsaturated keto group
US2461563A (en) * 1942-08-18 1949-02-15 Ciba Pharm Prod Inc Process for the degradation of the side-chain of steroids and steroids suitable therefor
US2520276A (en) * 1947-08-06 1950-08-29 Farinacci Nicholas Thomas Halogenated compounds of the cholenic acid series
US2541074A (en) * 1946-03-08 1951-02-13 Research Corp Preparation of derivatives of 3(alpha)-hydroxycholanic acid
US2590637A (en) * 1949-08-26 1952-03-25 Ciba Pharm Prod Inc Direct halogenation of steroids with an unsaturated side chain in 17-position and the dehydrohalogenation of resultant products
US2633451A (en) * 1951-05-22 1953-03-31 Wander Ag Dr A Photochemical production of 7-bromocholesteryl esters
US2647867A (en) * 1948-10-06 1953-08-04 Wander Ag Dr A Process for production of cholesteryl esters brominated in position 7
US3463795A (en) * 1967-01-13 1969-08-26 Shalom Sarel Unsaturated cycloheptano perhydro phenantrenes and their preparation

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2461910A (en) * 1942-08-18 1949-02-15 Ciba Pharm Prod Inc Process for the degradation of the side-chain of steroids and steroids suitable therefor
US2461912A (en) * 1942-08-18 1949-02-15 Ciba Pharm Prod Inc Process for the degradation of the side-chain of a steroid containing a nuclear alpha, beta-unsaturated keto group
US2461563A (en) * 1942-08-18 1949-02-15 Ciba Pharm Prod Inc Process for the degradation of the side-chain of steroids and steroids suitable therefor
US2541074A (en) * 1946-03-08 1951-02-13 Research Corp Preparation of derivatives of 3(alpha)-hydroxycholanic acid
US2461911A (en) * 1946-08-01 1949-02-15 Ciba Pharm Prod Inc Process for the degradation of the side-chain of steroids and steroids suitable therefor
US2520276A (en) * 1947-08-06 1950-08-29 Farinacci Nicholas Thomas Halogenated compounds of the cholenic acid series
US2647867A (en) * 1948-10-06 1953-08-04 Wander Ag Dr A Process for production of cholesteryl esters brominated in position 7
US2590637A (en) * 1949-08-26 1952-03-25 Ciba Pharm Prod Inc Direct halogenation of steroids with an unsaturated side chain in 17-position and the dehydrohalogenation of resultant products
US2633451A (en) * 1951-05-22 1953-03-31 Wander Ag Dr A Photochemical production of 7-bromocholesteryl esters
US3463795A (en) * 1967-01-13 1969-08-26 Shalom Sarel Unsaturated cycloheptano perhydro phenantrenes and their preparation

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