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

HRID 659104

反応式

HRID 659104 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
40 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-7ad11f1219ac4ba68972f8d9b5a47837
出典データセット
uspto-grants-2011_12
特許番号
US08080567B2

関連ノート

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