Sodium Hydroxide → 4-{[(3-Chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylic acid

HRID 852615ノート

反応式

HRID 852615 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([N:8](S(CCCCl)(=O)=O)[C:9]1[CH:17]=[C:16]([C:18]([O:20]C)=[O:19])[CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:22][CH3:23])(=[O:7])=[O:6].[OH-].[Na+]>CO>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([NH:8][C:9]1[CH:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:22][CH3:23])(=[O:6])=[O:7]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 69357512Methyl 4-{bis[(3-chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylate

生成物 1

HCID 693571504-{[(3-Chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylic acid収率 75%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl 4-{bis[(3-chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylate (D236) (1.8 g, 3.6 mmol, 1 equiv) in MeOH (100 ml) was added a 2N aqueous NaOH solution (20 ml, 40 mmol, excess) and the resulting mixture was stirred for 1 h. Most of MeOH was removed in vacuo and the residue partitioned between AcOEt and a 2N aqueous HCl solution. The two layers were separated and the aqueous phase was dried over MgSO4 and concentrated in vacuo to give 4-{[(3-chloropropyl)sulfonyl]amino}-1-ethyl-1H-indole-6-carboxylic acid (D240) (930 mg, 75%) as a brown oil which was used in the next step without further purification.

後処理

  1. customMost of MeOH was removed in vacuo
  2. customthe residue partitioned between AcOEt
  3. customThe two layers were separated
  4. dry with materialthe aqueous phase was dried over MgSO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-14b08453c6cb47548d0bc9c2e928fc29
出典データセット
uspto-grants-2007_08
特許番号
US07253198B2

反応ノート

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