IE34398L - Azetidinones - Google Patents
AzetidinonesInfo
- Publication number
- IE34398L IE34398L IE700941A IE94170A IE34398L IE 34398 L IE34398 L IE 34398L IE 700941 A IE700941 A IE 700941A IE 94170 A IE94170 A IE 94170A IE 34398 L IE34398 L IE 34398L
- Authority
- IE
- Ireland
- Prior art keywords
- aralkyl
- optionally substituted
- affords
- acyl
- july
- Prior art date
Links
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical class [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- -1 triphenylmethylamino Chemical group 0.000 abstract 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 238000005866 tritylation reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1,269,279. Azetidinones. BEECHAM GROUP Ltd. 20 July, 1970 [29 July, 1969], No. 37977/69. Heading C2C. Novel compounds I (including acid addition salts thereof and stereoisomers) where R is optionally substituted alkyl, aralkyl O alkenyl, R<SP>1</SP> is H, or optionally substituted alkyl, aralkyl or aryl or a salt forming ion, R<SP>2</SP> is H or optionally substituted aralkyl or acyl and R<SP>3</SP> is H or optionally substituted aralkyl, are made by reacting penicillanic acid derivatives (II), in anhydrous liquid medium, with a strong base which does not cleave the #-lactam ring, and with an alkylating, aralkylating or alkenylating agent to introduce R; II are such that the products I are those where R<SP>2</SP> is aralkyl (removal of aralkyl, e.g. trityl is conveniently removed utilizing p-toluene-sulphonic acid, affords I where R<SP>2</SP> is H; subsequent acylation affords I, where R<SP>2</SP> is acyl) and R<SP>1</SP> is alkyl, aralkyl or aryl (catalytic hydrogenation or hydrolysis accordingly affords the free acids I). The starting materials (II), e.g. benzyl and pmethoxybenzyl 6 - # - (triphenylmethylamino) penicillanates, are prepared, e.g. by the tritylation of the appropriate 6-aminopenicillanic acid esters.
[GB1269279A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB37977/69A GB1269279A (en) | 1969-07-29 | 1969-07-29 | Azetidinones and their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34398L true IE34398L (en) | 1971-01-29 |
| IE34398B1 IE34398B1 (en) | 1975-04-30 |
Family
ID=10400348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE941/70A IE34398B1 (en) | 1969-07-29 | 1970-07-20 | Azetidinones and their preparation |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT298672B (en) |
| BE (1) | BE754125A (en) |
| CA (1) | CA923910A (en) |
| CH (1) | CH538472A (en) |
| DE (1) | DE2037193A1 (en) |
| ES (1) | ES382211A1 (en) |
| FR (1) | FR2059575B1 (en) |
| GB (1) | GB1269279A (en) |
| IE (1) | IE34398B1 (en) |
| IL (1) | IL34965A0 (en) |
| NL (1) | NL7011045A (en) |
| ZA (1) | ZA705089B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE787329R (en) * | 1972-01-27 | 1973-02-08 | Beecham Group Ltd | HETEROCYCLIC COMPOUNDS WITH BETA-LACTAM CYCLE USEFUL FOR THE SYNTHESIS OF PENICILLINS AND CEPHALOSPORINS AND COMPOUNDS |
-
0
- BE BE754125D patent/BE754125A/xx unknown
-
1969
- 1969-07-29 CH CH1143670A patent/CH538472A/en not_active IP Right Cessation
- 1969-07-29 GB GB37977/69A patent/GB1269279A/en not_active Expired
-
1970
- 1970-07-20 IE IE941/70A patent/IE34398B1/en unknown
- 1970-07-21 IL IL34965A patent/IL34965A0/en unknown
- 1970-07-24 ZA ZA705089A patent/ZA705089B/en unknown
- 1970-07-24 NL NL7011045A patent/NL7011045A/xx unknown
- 1970-07-27 DE DE19702037193 patent/DE2037193A1/en active Pending
- 1970-07-27 ES ES382211A patent/ES382211A1/en not_active Expired
- 1970-07-28 AT AT686970A patent/AT298672B/en not_active IP Right Cessation
- 1970-07-28 CA CA089384A patent/CA923910A/en not_active Expired
- 1970-07-28 FR FR7027805A patent/FR2059575B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA923910A (en) | 1973-04-03 |
| ES382211A1 (en) | 1972-11-16 |
| AT298672B (en) | 1972-05-25 |
| FR2059575A1 (en) | 1971-06-04 |
| IL34965A0 (en) | 1970-09-17 |
| FR2059575B1 (en) | 1977-03-25 |
| DE2037193A1 (en) | 1971-02-11 |
| IE34398B1 (en) | 1975-04-30 |
| GB1269279A (en) | 1972-04-06 |
| CH538472A (en) | 1973-06-30 |
| NL7011045A (en) | 1971-02-02 |
| ZA705089B (en) | 1971-04-28 |
| BE754125A (en) | 1971-01-29 |
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