Carbon Dioxide → Ertapenem disodium

HRID 2067710노트

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HRID 2067710 반응식
[Na].[CH3:2][C@H:3]1[C:10]([S:11][C@@H:12]2[CH2:16][NH:15][C@H:14]([C:17]([NH:19][C:20]3[CH:21]=[CH:22][CH:23]=[C:24]([C:26]([OH:28])=[O:27])[CH:25]=3)=[O:18])[CH2:13]2)=[C:9]([C:29]([OH:31])=[O:30])[N:8]2[C@H:4]1[C@@H:5]([C@H:32]([OH:34])[CH3:33])[C:6]2=[O:7].C(=O)(O)[O-].[Na+:39].C(=O)=O>O.C(=O)(O)O.C1COCC1.CN(C=O)C.C(OCC)(=O)C.[Pd].[C]>[CH3:2][C@H:3]1[C:10]([S:11][C@@H:12]2[CH2:16][NH:15][C@H:14]([C:17]([NH:19][C:20]3[CH:25]=[C:24]([C:26]([O-:28])=[O:27])[CH:23]=[CH:22][CH:21]=3)=[O:18])[CH2:13]2)=[C:9]([C:29]([O-:31])=[O:30])[N:8]2[C@H:4]1[C@@H:5]([C@H:32]([OH:34])[CH3:33])[C:6]2=[O:7].[Na+:39].[Na+:39]

참가 물질

10

반응물 4

HCID 280Carbon DioxideHCID 150610ErtapenemHCID 516892Sodium BicarbonateHCID 5360545Sodium

생성물 1

HCID 150611Ertapenem disodium

시약·촉매·용매 5

HCID 178418390HCID 178418390, 화합물촉매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 21993411Carbonic acid--water (1/1)용매

실험 절차

To the solution of sodium salt of di-protected Ertapenem (IV) (50 g) in carbonic acid water (500 ml), THF (100 ml), DMF (25 ml) and ethyl acetate (1000 mL) and sodium bicarbonate (6.5 gm) in autoclave, Pd/carbon charged and subjected to hydrogenation with 8 to 10 Kg pressure at 5-10° C. After completion of reaction CO2 gas was purged, the reaction mass was filtered. The aqueous layer was separated, washed with ethyl acetate and the residual solvents in aqueous layer removed using degassing technique. The pH of the aqueous layer was adjusted using acetic acid to about 5.5-7.0 and slowly added into mixture of methanol (400 ml) and absolute isopropyl alcohol (6 L) under stirring. The precipitated Ertapenem disodium was filtered, washed with IPA and dried to yield amorphous form of Ertapenem disodium of formula (I). The solid obtained was optionally treated with methanol/isopropyl ether mixture at about −20° C. to yield Ertapenem disodium with low residual solvent content.

후처리

  1. customsubjected to hydrogenation with 8 to 10 Kg pressure at 5-10° C
  2. customwas purged
  3. filtrationthe reaction mass was filtered
  4. customThe aqueous layer was separated
  5. washwashed with ethyl acetate
  6. customthe residual solvents in aqueous layer removed
  7. customusing degassing technique
  8. additionslowly added into mixture of methanol (400 ml) and absolute isopropyl alcohol (6 L)
  9. filtrationThe precipitated Ertapenem disodium was filtered
  10. washwashed with IPA
  11. customdried

출처 및 근거

ORD 기록
ord-80d523d83936457d936e36a3d902943f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293894B2

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