Hydrochloric Acid → HCID 15725052, compound

HRID 846676Notes

Reaction equation

HRID 846676 reaction equation
[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]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 15724967HCID 15724967, compound

Product 1

HCID 15725052HCID 15725052, compoundYield 50.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 68666183HCID 68666183, compoundSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0a31572b5c554dc58b04c7fd3246fba5
Source dataset
uspto-grants-1992_08
Patent number
US05137909

Reaction notes

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