Hydrochloric Acid → Amoxicillin

HRID 918440

반응식

HRID 918440 반응식
ClC(OCC)=O.CN1CCOCC1.COC(C=C([NH:21][C@H:22]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[C:23]([O-:25])=O)C)=O.[Na+].[CH3:34][C:35]1([CH3:47])[S:39][C@@H:38]2[C@H:40]([NH2:43])[C:41](=[O:42])[N:37]2[C@H:36]1[C:44]([OH:46])=[O:45].Cl>CC(C)CC(=O)C.O>[CH3:34][C:35]1([CH3:47])[S:39][C@@H:38]2[C@H:40]([NH:43][C:23]([C@H:22]([NH2:21])[C:26]3[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=3)=[O:25])[C:41](=[O:42])[N:37]2[C@H:36]1[C:44]([OH:46])=[O:45]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 110826-Aminopenicillanic acidHCID 57376483sodium (R)-N-(1-methoxycarbonyl propen-2-yl)-alpha-amino-p-hydroxyphenylacetate

생성물 1

HCID 33613Amoxicillin수율 75.5%

시약·촉매·용매 2

HCID 962Water용매HCID 7909Methyl Isobutyl Ketone용매2회

실험 절차

Meanwhile, 4-methylpentan-2-one (70 ml) was stirred and cooled to 0° and ethyl chloroformate (2.0 ml, 0.0208 mole) and a 1% solution of N-methylmorpholine in 4-methylpentan-2-one (3 ml) was added. The solution was cooled to -5° and sodium (R)-N-(1-methoxycarbonyl propen-2-yl)-α-amino-p-hydroxyphenylacetate (5.87 g, 0.02 mole) was added. The suspension was stirred at 0° to -5° for 30 minutes, cooled to -30° and then added to the solution of 6-APA prepared above. The mixture was stirred at -30° for 45 minutes when water (50 ml) was added. The stirred two-phase mixture was acidified to pH 1.1 with concentrated hydrochloric acid and stirred at 0° to 2° for 75 minutes, during which time a white precipitate separated. The mixture was adjusted to pH 5.2 with 10% aqueous potassium hydroxide solution, and the white suspension was stirred and cooled to 0° for 1 hour and filtered. The filter was washed with ice-cold water (20 ml) and ethyl acetate (20 ml), and the solid was air dried at 35° to give amoxycillin trihydrate (6.33 g, 75.5% th.), [α]D25 + 237° (c 0.9; 0.1 N HCl).

후처리

  1. temperaturecooled to 0°
  2. temperatureThe solution was cooled to -5°
  3. temperaturecooled to -30°
  4. customprepared above
  5. additionwas added
  6. stirringstirred at 0° to 2° for 75 minutes, during which time a white precipitate
  7. customseparated
  8. stirringthe white suspension was stirred
  9. temperaturecooled to 0° for 1 hour
  10. filtrationfiltered
  11. washThe filter was washed with ice-cold water (20 ml) and ethyl acetate (20 ml)
  12. customdried at 35°

출처 및 근거

ORD 기록
ord-dccb04c1e90d4ecf84595d65a1310024
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03971775

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