Water → HCID 13127783, 화합물

HRID 236218노트

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HRID 236218 반응식
C(N(CCCC)CCCC)CCC.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:19][C:20]([NH:22][C@@H:23]1[C:35](=[O:36])[N:25]2[C:26]([C:32]([OH:34])=[O:33])=[C:27]([CH2:30]O)[CH2:28][S:29][C@H:24]12)=[O:21].[SH:37][C:38]1[N:42]([CH3:43])[N:41]=[N:40][N:39]=1.O>C(OCC)(=O)C>[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:19][C:20]([NH:22][C@@H:23]1[C:35](=[O:36])[N:25]2[C:26]([C:32]([OH:34])=[O:33])=[C:27]([CH2:30][S:37][C:38]3[N:42]([CH3:43])[N:41]=[N:40][N:39]=3)[CH2:28][S:29][C@H:24]12)=[O:21]

참가 물질

5

반응물 3

HCID 962WaterHCID 70378458HCID 70378458, 화합물HCID 178482017HCID 178482017, 화합물

생성물 1

HCID 13127783HCID 13127783, 화합물수율 84.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

반응 조건

온도
-20 °C

실험 절차

To 10 ml of ethyl acetate were added 0.540 g of 7β-(2-thienylacetamido)-3-hydroxymethyl-3-cephem-4-carboxylic acid tri-n-butylamine salt and 0.175 g of 5-mercapto-1-methyl-1H tetrazole and, under cooling at -20° C. and stirring, a solution of 0.370 g of methyl o-phenylene phosphorochloridate in 5 ml of ethyl acetate was added. The mixture was stirred under ice-cooling for 1.5 hours and 10 ml of water was added. After phase separation, 20 ml of water was added to the organic layer and the mixture was adjusted to pH 9.0. The aqueous layer was taken and washed with 5 ml of ethyl acetate. To the aequous layer was added 20 ml of ethyl acetate and the mixture was adjusted to pH 2.0. After phase separation, the organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was distilled off under reduced pressure and ether was added. The powdery precipitate was collected by filtration to give 0.380 g (yield 84.1%) of 7β-(2-thienylacetamido)-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid. The IR and NMR spectra of this product were identical with those of the authentic sample.

후처리

  1. stirringThe mixture was stirred under ice-
  2. temperaturecooling for 1.5 hours
  3. customAfter phase separation, 20 ml of water
  4. additionwas added to the organic layer
  5. washwashed with 5 ml of ethyl acetate
  6. additionTo the aequous layer was added 20 ml of ethyl acetate
  7. customAfter phase separation
  8. washthe organic layer was washed with saturated aqueous sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe ethyl acetate was distilled off under reduced pressure and ether
  11. additionwas added
  12. filtrationThe powdery precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-99d7379b852643448ef04fc9156addcb
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04642365

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