Hydrochloric Acid → [4-chloro-2-[4-(phenylsulfonyl)-1-piperazinyl]phenoxy]-acetic Acid

HRID 38263ノート

反応式

HRID 38263 の反応式
Cl.[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11]CC)=[O:10])=[C:5]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:4]=1.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.Cl>C1COCC1>[Cl:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([OH:11])=[O:10])=[C:5]([N:16]2[CH2:17][CH2:18][N:19]([S:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:30])=[O:29])[CH2:20][CH2:21]2)[CH:4]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 86631058[4-chloro-2-(1-piperazinyl)phenoxy]-acetic Acid, Ethyl Ester Hydrochloride Salt

生成物 1

HCID 11718521[4-chloro-2-[4-(phenylsulfonyl)-1-piperazinyl]phenoxy]-acetic Acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of the product from step c) (0.34 g) and benzenesulfonyl chloride (0.11 ml) in THF (3 ml) was added triethylamine (0.42 ml) dropwise. After 5 min, further THF (3 ml) was added and the reaction stirred for 16 h. It was poured into 2M HCl and extracted with ethyl acetate. The organic layer was separated and washed with sat aqueous sodium bicarbonate solution, brine, dried (Na2SO4) and the solvent removed in vacuo. The residue was stirred in THF (2 ml) and 4M NaOH (4 ml) for 16 h. After acidification to pH 3, the aqueous layer was extracted with ethyl acetate. The organic layer was separated and the solvent removed in vacuo. Purification by RPHPLC (symmetry column) gave the title product as a white foam (0.12 g).

後処理

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with sat aqueous sodium bicarbonate solution, brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed in vacuo
  6. stirringThe residue was stirred in THF (2 ml)
  7. wait4M NaOH (4 ml) for 16 h
  8. extractionAfter acidification to pH 3, the aqueous layer was extracted with ethyl acetate
  9. customThe organic layer was separated
  10. customthe solvent removed in vacuo
  11. customPurification by RPHPLC (symmetry column)

出典と根拠

ORDレコード
ord-b5c188c6c2d7447787bd98aa399e7bf2
出典データセット
uspto-grants-2013_09
特許番号
US08524715B2

反応ノート

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