Hydrochloric Acid → [4-Acetylamino-3-(biphenyl-4-ylsulfanyl)-2-methyl-indol-1-yl]-acetic Acid

HRID 18497노트

반응식

HRID 18497 반응식
C([O:3][C:4](=[O:20])[CH2:5][N:6]1[C:14]2[C:9](=[C:10]([NH:15][C:16](=[O:18])[CH3:17])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:19])C.[C:21]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][C:24]([SH:27])=[CH:23][CH:22]=1.II.[OH-].[Na+].Cl>CN(C=O)C.O>[C:16]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[C:8]([S:27][C:24]1[CH:23]=[CH:22][C:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:26][CH:25]=1)=[C:7]([CH3:19])[N:6]2[CH2:5][C:4]([OH:3])=[O:20])(=[O:18])[CH3:17]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 14798Sodium HydroxideHCID 27604144-Phenylbenzene-1-thiolHCID 59431286Ethyl 2-(4-acetamido-2-methyl-1H-indol-1-yl)acetate

생성물 1

HCID 24850440[4-Acetylamino-3-(biphenyl-4-ylsulfanyl)-2-methyl-indol-1-yl]-acetic Acid수율 37.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of (4-acetylamino-2-methyl-indol-1-yl)-acetic acid ethyl ester (0.27 g) and biphenyl-4-thiol (0.19 g) in DMF (5 ml) was added iodine (0.25 g). After stirring at RT overnight 1M NaOH (3 ml) was added and the reaction stirred at RT for a further 12 hours. The reaction was poured into water, the pH adjusted to 3 using 1M HCl and the organics extracted with EtOAc. The EtOAc extractions were combined, washed with brine, dried (MgSO4) and evaporated under reduced pressure to give crude material. Purification using RPHPLC gave the title compound as a pink solid (0.16 g).

후처리

  1. additionwas added
  2. extractionthe organics extracted with EtOAc
  3. extractionThe EtOAc extractions
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto give crude material
  8. customPurification

출처 및 근거

ORD 기록
ord-01bbb7a7e0ec4ddea8d8826b83d044c8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741360B2

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