Process for producing diazabicyclooctane derivative
A process for producing a compound represented by a Formula (III), including reacting a compound of the following formula with a compound selected from the group consisting of 1-hydroxypyrrolidine-2,5-dione, 2-hydroxy-3a,4,7,7a-tetrahydro-1H-isoindol-1,3(2H)-dione, 2-hydroxyhexahydro-1H-isoindol-1,3(2H)-dione and 4-hydroxy-4-azatricyclo[5.2.1.0 2,6 ]dec-8-ene-3,5-dione, carrying out a carbonylation to obtain a compound of the following formula removing the NH protecting group P and treating the resultant compound with a base to produce a compound represented by the following formula wherein OBn is benzyloxy and R 2 is hydrogen, ClCO— or Cl 3 COCO—.
1. A process for producing a compound represented by a Formula (III), comprising: reacting a compound represented by the following Formula (I):
with a compound selected from the group consisting of 1-hydroxypyrrolidine-2,5-dione, 2-hydroxy-3a,4,7,7a-tetrahydro-1H-isoindol-1,3(2H)-dione, 2-hydroxyhexahydro-1H-isoindol-1,3(2H)-dione and 4-hydroxy-4-azatricyclo[5.2.1.0 2,6 ]dec-8-ene-3,5-dione, allowing a carbonylating agent selected from the group consisting of phosgene, diphosgene and triphosgene to act on the resultant compound to obtain a compound represented by the following Formula (II):
removing the protecting group P and treating the resultant compound with a base to produce a compound represented by the following Formula (III):
wherein in said Formulas (I), (II) and (III), OBn is benzyloxy; P is an NH protecting group capable of being removed with an acid; R 1 is 2,5-dioxopyrrolidin-1-yl, 1,3-dioxo-3a,4,7,7a-tetrahydro-1H-isoindol-2(3H)-yl, 1,3-dioxohexahydro-1H-isoindol-2(3H)-yl or 3,5-dioxo-4-azatricyclo[5.2.1.0 2,6 ]dec-8-en-4-yl and R 2 is hydrogen, ClCO— or Cl 3 COCO—.
2. The process according to claim 1 , wherein P is tert-butoxycarbonyl.
3. The process according to claim 1 , wherein R 1 is 2,5-dioxopyrrolidin-1-yl.
4. The process according to claim 1 , wherein R 1 is 1,3-dioxo-3a,4,7,7a-tetrahydro-1H-isoindol-2(3H)-yl.
5. The process according to claim 1 , wherein R 1 is 1,3-dioxohexahydro-1H-isoindol-2(3H)-yl.
6. The process according to claim 1 , wherein R 1 is 3,5-dioxo-4-azatricyclo[5.2.1.0 2,6 ] dec-8-en-4-yl.
7. A process for producing a compound represented by a Formula (III), comprising: allowing a carbonylating agent selected from the group consisting of phosgene, diphosgene and triphosgene to act on a compound represented by the following Formula (II):
removing the protecting group P and treating the resultant compound with a base to produce the compound represented by the following Formula (III):
wherein in said Formulas (II) and (III), OBn is benzyloxy; P is an NH protecting group capable of being removed with an acid; R 1 is 2,5-dioxopyrrolidin-1-yl, 1,3-dioxo-3a,4,7,7a-tetrahydro-1H-isoindol-2(3H)-yl, 1,3-dioxohexahydro-1H-isoindol-2(3H)-yl or 3,5-dioxo-4-azatricyclo[5.2.1.0 2,6 ]dec-8-en-4-yl and R 2 is hydrogen.
8. The process according to claim 7 , wherein P is tert-butoxycarbonyl.
9. The process according to claim 7 , wherein R 1 is 2,5-dioxopyrrolidin-1-yl.
10. The process according to claim 7 , wherein R 1 is 1,3-dioxo-3a,4,7,7a-tetrahydro-1H-isoindol-2(3H)-yl.
11. The process according to claim 7 , wherein R 1 is 1,3-dioxohexahydro-1H-isoindol-2(3H)-yl.
12. The process according to claim 7 , wherein R 1 is 3,5-dioxo-4-azatricyclo[5.2.1.0 2,6 ] dec-8-en-4-yl.