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

HRID 852615노트

반응식

HRID 852615 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-14b08453c6cb47548d0bc9c2e928fc29
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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