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Water → HCID 13338941, 화합물

HRID 978896
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HRID 978896 반응식
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:12]/[OH:13])/[C:8]([O:10][CH3:11])=[O:9])[N:6]=1.C(N(CC)CC)C.[C:21](Cl)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O>[C:21]([NH:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:12]/[OH:13])/[C:8]([O:10][CH3:11])=[O:9])[N:6]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 6411353Methyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate

생성물 1

HCID 13338941HCID 13338941, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
-30 °C

실험 절차

In 10 ml of N,N-dimethylformamide is dissolved 4.62 g of methyl 2-(2-amino-4-thiazolyl)-(Z)-2-hydroxyiminoacetate, followed by addition of 3 ml of triethylamine. Then, under stirring at -30° C., 6.42 g of trityl chloride is added over one hour. The mixture is further stirred at that temperature for one hour and, then at 15° C. for an additional 2 hours. To this reaction mixture is added 200 ml of water, followed by extraction with 200 ml of ethyl acetate. The ethyl acetate extract is washed twice with 200 ml portions of water and dried over anhydrous sodium sulfate. The solvent is then distilled off. The residue is purified by column chromatography [silica gel: 100 g; eluent:hexane-ethyl acetate (1:1)] and the resultant crystals are recrystallized from ethyl acetate to give methyl 2-(2-tritylamino-4-thiazolyl)-(Z)-2-hydroxyiminoacetate as colorless granules, m.p. 294°-205° C.

후처리

  1. stirringThe mixture is further stirred at that temperature for one hour
  2. extractionfollowed by extraction with 200 ml of ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washis washed twice with 200 ml portions of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent is then distilled off
  7. customThe residue is purified by column chromatography [silica gel: 100 g; eluent:hexane-ethyl acetate (1:1)]
  8. customthe resultant crystals are recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-db0fff7e9070492b854107c4a4ba4eda
출처 데이터셋
uspto-grants-1987_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04665067

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