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Water → HCID 76577930, 화합물

HRID 240322
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HRID 240322 반응식
[C:1]([C:3]1[N:4]=[C:5]2[C:18](=[N:19][OH:20])[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:6]2=[N:7][C:8]=1[C:9]([NH2:11])=[O:10])#[N:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:27]([O:29][C:30](=[O:37])[CH2:31][NH:32][C:33](=[O:36])[CH2:34]Br)[CH3:28].O>CN(C=O)C>[CH2:27]([O:29][C:30](=[O:37])[CH2:31][NH:32][C:33](=[O:36])[CH2:34][O:20][N:19]=[C:18]1[C:5]2[C:6](=[N:7][C:8]([C:9](=[O:10])[NH2:11])=[C:3]([C:1]#[N:2])[N:4]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]1=2)[CH3:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 96555N-(Bromoacetyl)glycine, ethyl esterHCID 178510554HCID 178510554, 화합물

생성물 1

HCID 76577930HCID 76577930, 화합물수율 17.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 33 (212 mg, 0.80), Cs2CO3 (260 mg, 0.80) in DMF (15 ml), 39 (200 mg, 0.89 mmol) was added portionwise and the mixture was stirred at room temperature for 2 days. H2O (30 ml) was added and the suspension was extracted with CH2Cl2 (70 ml). The organic phase was dried over Na2SO4 and the solvent was evaporated under reduced pressure. The crude was purified by flash chromatography (CH2Cl2/MeOH 9:1) affording 40 (56 mg, 17%) as yellow-brown solid. 1H NMR (300 MHz, DMSO d6): δ 8.78 (m, 2H), 8.12 (bs, 1H), 8.05-7.78 (m, 3H), 7.67 (m, 1H), 4.72 and 4.69 (s, 2H), 4.10 (q, 2H), 3.92 and 3.90 (s, 2H), 1.19 (t, 3H). ESI+MS: calcd for C19H16N6O5: 408.38; found: 409.1 (MH+).

후처리

  1. additionwas added portionwise
  2. extractionthe suspension was extracted with CH2Cl2 (70 ml)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent was evaporated under reduced pressure
  5. customThe crude was purified by flash chromatography (CH2Cl2/MeOH 9:1)

출처 및 근거

ORD 기록
ord-7febceee04f14e77a96b4dbd71eaf4e4
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08648076B2

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