Hydrochloric Acid → HCID 15725052、化合物

HRID 846676ノート

反応式

HRID 846676 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[S:10][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:15])[C:12](O)=[O:13].ClC(OCC)=O.[BH4-].[Na+].Cl>O1CC(CCN)C(CCN)C1CCN.O1CCCC1.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[S:10][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:15])[CH2:12][OH:13]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 15724967HCID 15724967、化合物

生成物 1

HCID 15725052HCID 15725052、化合物収率 50.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 68666183HCID 68666183、化合物溶媒

実験手順

To a solution (20 ml) of 2-(1H-indol-2-yl)thio-2-phenylpropionic acid (5.0 g) in anhydrous tetrahydrofuran triethylamine (1.7 g) was added. Thereafter, a solution (8 ml) of ethyl chloroformate (1.8 g) in anhydrous tetrahydrofuran was added dropwise under argon atmosphere with ice cooling. The mixture was stirred at that temperature for one hour. The deposited salt was filtered off to prepare a solution of a mixed acid anhydride in tetrahydrofuran. This mixed acid anhydride solution was added to a suspension of sodium borohydride (2.2 g) in water (30 ml) within the temperature range of from 10° to 15° C., and the mixture was stirred at that temperature for 4 hours. The reaction solution was acidified by adding concentrated hydrochloric acid, and extracted by ethyl acetate. The organic layer was washed with water, and a saturated aqueous sodium chloride solution, and was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (diluting solvent: methylene chloride), and further recrystallized from acetonitrile to give 2.4 g (yield: 48 %) of the product compound as a colorless powder. The melting point was 125.5°-127° C.

後処理

  1. filtrationThe deposited salt was filtered off
  2. customto prepare a solution of a mixed acid anhydride in tetrahydrofuran
  3. stirringthe mixture was stirred at that temperature for 4 hours
  4. extractionextracted by ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, and was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (diluting solvent: methylene chloride)
  9. customfurther recrystallized from acetonitrile

出典と根拠

ORDレコード
ord-0a31572b5c554dc58b04c7fd3246fba5
出典データセット
uspto-grants-1992_08
特許番号
US05137909

反応ノート

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