HCID 68004074、化合物 → (1H-Indol-3-ylsulfanyl)-acetic acid

HRID 1621270ノート

反応式

HRID 1621270 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([S:10][CH2:11][C:12]([O:14]C)=[O:13])=[CH:2]1>O1CCCC1.[Li+].[OH-].ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([S:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:2]1

参加物

5

反応物 1

HCID 68004074HCID 68004074、化合物

生成物 1

HCID 590707(1H-Indol-3-ylsulfanyl)-acetic acid収率 38%

試薬・触媒・溶媒 3

HCID 3939Lithium Hydroxide溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 2-((1H-indol-3-yl)thio)acetate from Step A was dissolved in a mixture of tetrahydrofuran (20 mL) and 2.0 M aqueous LiOH (15 mL), then stirred vigorously at ambient temperature for 30 min. Tetrahydrofuran was removed in vacuo, the aqueous layer neutralized with 1.2 N HCl and extracted with CH2Cl2. The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo to produce an oily residue. Upon diluting the residue in dichloromethane a solid formed which was filtered and dried to yield the desired product (2.00 grams, 9.65 mmol, 38% yield over 2 steps). LCMS>99% at 254 nm, RT=1.02 min, m/z=208 (M+1).

後処理

  1. customTetrahydrofuran was removed in vacuo
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customto produce an oily residue
  6. customformed which
  7. filtrationwas filtered
  8. customdried

出典と根拠

ORDレコード
ord-7081289dd766440c83c3699322d7769c
出典データセット
uspto-grants-2014_07
特許番号
US08772509B2

反応ノート

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