Potassium → 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, 4-oxide

HRID 904060노트

반응식

HRID 904060 반응식
[K].O(CC(NC1C(=O)N2C(C(O)=O)C(C)(C)S[C@H]12)=O)C1C=CC=CC=1.OO[S:28]([O-:30])=O.[K+].[CH3:32][C:33]1([CH3:54])S[C@@H:36]2[C@H:38]([NH:41][C:42]([CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[O:43])[C:39](=[O:40])[N:35]2[C@H:34]1[C:51]([O-:53])=[O:52].[K+]>O>[CH3:32][C:33]1([CH3:54])[S:28](=[O:30])[C@@H:36]2[C@H:38]([NH:41][C:42]([CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)=[O:43])[C:39](=[O:40])[N:35]2[C@H:34]1[C:51]([OH:53])=[O:52]

참가 물질

6

반응물 4

HCID 5462222PotassiumHCID 123738936-(2-Phenoxyacetamido)-2,2-dimethylpenam-3-carboxylic acidHCID 23664709Penicillin G PotassiumHCID 23707502Potassium hydroxy sulfite

생성물 1

HCID 1074964-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, 4-oxide수율 98%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To 50 ml. of water were added 19.4 grams (50 millimoles) of the potassium salt of 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylic acid. A solution of 20 grams (65 millimoles active oxygen) of Oxone® in 100 ml. water was added dropwise to the penicillin solution over a 45 minute period. The mixture was stirred for about 10 minutes at room temperature. The resulting precipitate was collected by filtration and washed with 25 ml. of water. The precipitate was dried in vacuo at 40° C. overnight to afford 17.95 grams (98%) of the corresponding penicillin sulfoxide. Analysis of the product by high performance liquid chromatography (HPLC) indicated the presence of 23.0% of the α-isomer and 74.1% of the β-isomer.

후처리

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with 25 ml
  3. customThe precipitate was dried in vacuo at 40° C. overnight

출처 및 근거

ORD 기록
ord-650932ad34d041a6a44cbf34afdc1dbf
출처 데이터셋
uspto-grants-1980_10
특허 번호
US04230620

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