Dicyclohexylcarbodiimide → HCID 53709484、化合物

HRID 1980425ノート

反応式

HRID 1980425 の反応式
C1(N=C=NC2CCCCC2)CCCCC1.[NH2:16][CH:17]1[C:24](=[O:25])[N:23]2[CH:18]1[S:19](=[O:56])[CH2:20][C:21]([C:42]1[S:46][C:45]([NH:47][C:48](=[O:55])[C:49]3[CH:54]=[CH:53][CH:52]=[N:51][CH:50]=3)=[N:44][CH:43]=1)=[C:22]2[C:26]([O:28][CH:29]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].[CH3:57][O:58][N:59]=[C:60]([C:64]1[N:65]=[C:66]([NH:69][C:70]([C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)([C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)[C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[S:67][CH:68]=1)[C:61](O)=[O:62].ON1C2C=CC=CC=2N=N1>CN(C)C=O>[CH:29]([O:28][C:26]([C:22]1[N:23]2[CH:18]([S:19](=[O:56])[CH2:20][C:21]=1[C:42]1[S:46][C:45]([NH:47][C:48](=[O:55])[C:49]3[CH:54]=[CH:53][CH:52]=[N:51][CH:50]=3)=[N:44][CH:43]=1)[CH:17]([NH:16][C:61](=[O:62])[C:60](=[N:59][O:58][CH3:57])[C:64]1[N:65]=[C:66]([NH:69][C:70]([C:77]3[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=3)([C:83]3[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=3)[C:71]3[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=3)[S:67][CH:68]=1)[C:24]2=[O:25])=[O:27])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724510(Z)-2-(2-Tritylaminothiazol-4-yl)-2-methoxyiminoacetic acidHCID 20402453HCID 20402453、化合物

生成物 1

HCID 53709484HCID 53709484、化合物収率 128.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N,N'-Dicyclohexylcarbodiimide (1.24 g) is added to a solution, cooled to +5° C., of 7-amino-2-benzhydry-loxycarbonyl-8-oxo-3-(2-nicotinoylaminothiazol-5-yl)-5-thia- 1-azabicyclo[4.2.0]oct-2-ene 5-oxide (2.8g), the syn isomer of 2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetic acid (2.66 g) and 1-hydroxybenzotriazole (0.82 g) in N,N-dimethylformamide (20 cc), and the reaction mixture is then stirred for 1 hour at +5° C. and then for 64 hours at 20° C; after filtration, the reaction mixture is diluted with chloroform (200 cc) and washed with a 5% strength solution of sodium bicarbonate (100 cc), water (100 cc) and then a saturated solution of sodium chloride (100 cc). After drying over magnesium sulphate, the organic phase is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. to give the crude product (5 g). This crude product (10 g) is chromatographed on a column containing silica gel (0.2-0.06 mm) (250 cc), elution being carried out successively with a mixture of methylene chloride and ethyl acetate (75/25 by volume) (1 liter), then a mixture of methylene chloride and ethyl acetate (50/50 by volume) (1 liter) and then ethyl acetate (2 liters) and a mixture of ethyl acetate and methanol (80/20 by volume) (1 liter) and 100 cc fractions being collected. Fractions 19 to 33 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. to give the syn isomer of 2-benzhydryLoxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-3-(2-nicotinoylaminothiazol-5-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene 5-oxide (6.2 g) in the form of an orange solid.

後処理

  1. filtrationafter filtration
  2. additionthe reaction mixture is diluted with chloroform (200 cc)
  3. washwashed with a 5% strength solution of sodium bicarbonate (100 cc), water (100 cc)
  4. dry with materialAfter drying over magnesium sulphate
  5. concentrationthe organic phase is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C.
  6. customto give the crude product (5 g)
  7. customThis crude product (10 g) is chromatographed on a column
  8. additioncontaining
  9. washsilica gel (0.2-0.06 mm) (250 cc), elution
  10. additionbeing carried out successively with a mixture of methylene chloride and ethyl acetate (75/25 by volume) (1 liter)
  11. additiona mixture of methylene chloride and ethyl acetate (50/50 by volume) (1 liter)
  12. additionethyl acetate (2 liters) and a mixture of ethyl acetate and methanol (80/20 by volume) (1 liter) and 100 cc fractions
  13. custombeing collected
  14. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C.

出典と根拠

ORDレコード
ord-a11277e9c97e47959e00d1d15813ed05
出典データセット
uspto-grants-1985_04
特許番号
US04508717

反応ノート

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