Hydrochloric Acid → 3-{3-[(Dibenzofuran-2-carbonyl)-amino]phenyl}-acrylic acid

HRID 659104

반응식

HRID 659104 반응식
C([O:3][C:4](=[O:29])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([C:16]2[CH:28]=[CH:27][C:19]3[O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:18]=3[CH:17]=2)=[O:15])[CH:8]=1)C.CO.C1COCC1.Cl>CC(OC)(C)C>[CH:17]1[C:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[O:20][C:19]=2[CH:27]=[CH:28][C:16]=1[C:14]([NH:13][C:9]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]([OH:29])=[O:3])[CH:12]=[CH:11][CH:10]=1)=[O:15]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 684136723-{3-[(Dibenzofuran-2-carbonyl)-amino]-phenyl}-acrylic acid ethyl ester

생성물 1

HCID 684122573-{3-[(Dibenzofuran-2-carbonyl)-amino]phenyl}-acrylic acid

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
40 °C

실험 절차

The ester (19) (46 mg, 0.12 mmol) was hydrolysed using Method C, except that MeOH (1 mL) and THF (1 mL) were used, and the reaction mixture was heated to 40° C. for 1 hour. After the reaction, TBME was added and the mixture acidified using 6N HCl. The aqueous was extracted with more TBME (×3), EtOAc (×3), dried (MgSO4) and the solvent concentrated in vacuo. The crude solid was triturated with DCM, filtered, washed with heptane and dried to give the title compound. Yield: 34 mg, 81%; LC-MS tr 2.08 min; HPLC Purity: 100%; MS (ES+) m/z 358 (M+H); 1H NMR (400 MHz; DMSO): δ 6.60 (d, 1H), 7.55-7.75 (m, 5H), 7.9 (d, 1H), 7.95-8.05 (m, 2H), 8.25 (s, 1H), 8.30 (d, 1H), 8.40 (d, 1H), 8.95 (s, 1H), 10.65 (s, 1H)

후처리

  1. additionwas added
  2. extractionThe aqueous was extracted with more TBME (×3), EtOAc (×3)
  3. dry with materialdried (MgSO4)
  4. concentrationthe solvent concentrated in vacuo
  5. customThe crude solid was triturated with DCM
  6. filtrationfiltered
  7. washwashed with heptane
  8. customdried

출처 및 근거

ORD 기록
ord-7ad11f1219ac4ba68972f8d9b5a47837
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080567B2

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