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

HRID 18497ノート

反応式

HRID 18497 の反応式
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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-01bbb7a7e0ec4ddea8d8826b83d044c8
出典データセット
uspto-grants-2010_06
特許番号
US07741360B2

反応ノート

読み込み中…