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2-Mercaptobenzoic Acid → Ethyl 2-(4-acetamido-2-methyl-1H-indol-1-yl)acetate

HRID 2246711
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HRID 2246711 반응식
[C:1]([OH:10])(=[O:9])[C:2]1C(=CC=CC=1)S.[C:11]([NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17](SC1C=CC(Cl)=CC=1)[C:18]([CH3:28])(CC(O)=O)[NH:19]2)(=[O:13])[CH3:12].F[C:38](F)(F)[C:39](O)=O>>[C:11]([NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[C:18]([CH3:28])[N:19]2[CH2:2][C:1]([O:10][CH2:38][CH3:39])=[O:9])(=[O:13])[CH3:12]
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참가 물질

4

반응물 3

HCID 54432-Mercaptobenzoic Acid2회HCID 6422Trifluoroacetic acidHCID 669653494-(acetylamino)-3-[(4-chlorophenyl)thio]-2-methyl-1H-indole-acetic acid

생성물 1

HCID 59431286Ethyl 2-(4-acetamido-2-methyl-1H-indol-1-yl)acetate

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온도
60 °C

실험 절차

Thiosalicylic acid was added to a solution of the product from Example 1 part (iv) (474 mg) in trifluoroacetic acid (10 ml) was added thiosalicylic acid (351 mg) and the resulting suspension was heated to 60° C. for 4 hours. The mixture was concentrated in vacuo and the residue dissolved in EtOAc and washed with NaHCO3 (aq), brine, dried (MgSO4) and evaporated to give crude material. Purification by column chromatography (50% EtOAc/hexane as eluent) gave the sub-title compound (0.13 g).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in EtOAc
  3. washwashed with NaHCO3 (aq), brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give crude material
  7. customPurification by column chromatography (50% EtOAc/hexane as eluent)

출처 및 근거

ORD 기록
ord-f0a0cca00f984f35a7fdf98d11e93854
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07687535B2

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