4-Hydroxybenzaldehyde → HCID 58043115, 화합물

HRID 1035240노트

반응식

HRID 1035240 반응식
CS([O:5][CH:6]1[CH2:9][N:8]([C:10]([C:12]2[O:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][N:16]=2)=[O:11])[CH2:7]1)(=O)=O.O[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CC(N(C)C)=O>[C:17]1([C:14]2[O:13][C:12]([C:10]([N:8]3[CH2:9][CH:6]([O:5][C:24]4[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=4)[CH2:7]3)=[O:11])=[N:16][N:15]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 10796Cesium carbonateHCID 580430991-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

생성물 1

HCID 58043115HCID 58043115, 화합물수율 66.1%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
110 °C

실험 절차

Intermediate 53B (5.0 g, 15.5 mmol) was dissolved in DMA (40 mL) and 4-hydroxybenzaldehyde (2.17 g, 17.8 mmol) was added followed by Cs2CO3 (5.8 g, 17.8 mmol). The mixture was stirred at 110° C. for 5 h. Water was added and the mixture was extracted trice with DCM. The solution was filtered through a phase separator and the solvent was removed by evaporation. Ether was added to the residue and the formed solid was filtered and washed with ether. The product was dried in vacuo to give 3.58 g (66%) of 71A as a beige solid. 1H NMR (500 MHz, CDCl3): δ 4.37 (m, 1H), 4.70 (m, 1H), 4.79 (m, 1H), 5.18 (m, 2H), 6.91 (d, 2H), 7.53 (t, 2H), 7.60 (t, 1H), 7.87 (d, 2H), 8.16 (d, 2H), 9.92 (s, 1H).

후처리

  1. extractionthe mixture was extracted trice with DCM
  2. filtrationThe solution was filtered through a phase separator
  3. customthe solvent was removed by evaporation
  4. additionEther was added to the residue
  5. filtrationthe formed solid was filtered
  6. washwashed with ether
  7. customThe product was dried in vacuo

출처 및 근거

ORD 기록
ord-d57330169b324064a880f5c671d19ecc
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546375B2

반응 노트

불러오는 중…