Hydrochloric Acid → t-butyl [(1R)-2-chloro-1-(4-iodobenzyl)ethyl]carbamate

HRID 747734ノート

反応式

HRID 747734 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=1)[C:10](OC)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].Cl.C(N(CC)CC)C.CS([Cl:36])(=O)=O.[Cl-].[Li+]>O.CN(C)C=O.O1CCCC1.CO>[Cl:36][CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=1

参加物

11

反応物 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 53885913N-((1,1-Dimethylethoxy)carbonyl)-4-iodo-D-phenylalanine methyl ester

生成物 1

HCID 86760709t-butyl [(1R)-2-chloro-1-(4-iodobenzyl)ethyl]carbamate

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

25 ml of methanol and 25 ml of tetrahydrofuran were added to 6.2 g (18 mmol) of methyl (2R)-t-butoxycarbonylamino-3-(4-iodophenyl)propionate. 3.44 g (91 mmol) of sodium borohydride was added to the resultant mixture under cooling with ice, and they were stirred for 17 hours. The reaction liquid was slowly poured into 1 N hydrochloric acid. After the extraction with ethyl acetate, the organic layer was successively washed with water, 1 N hydrochloric acid, 1 N sodium hydroxide and saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated. 50 ml of dichloromethane was added to the residue. Then, 5.02 ml (36 mmol) of triethylamine and 3.09 g (27 mmol) of methanesulfonyl chloride were added to the resultant mixture under cooling with ice, and they were stirred for 30 minutes. The temperature was elevated to room temperature, and the mixture was stirred for 15 hours. The reaction liquid was diluted with water. After the extraction with dichloromethane, the organic layer was successively washed with 1 N hydrochloric acid, 1 N sodium hydroxide and saturated aqueous NaCl solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. 40 ml of dimethylformamide and 3.85 g (91 mmol) of lithium chloride were added to the residue, and they were stirred at 50° C. for 19 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water and saturated aqueous NaCl solution. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

後処理

  1. temperatureunder cooling with ice, and they
  2. customThe reaction liquid
  3. extractionAfter the extraction with ethyl acetate
  4. washthe organic layer was successively washed with water, 1 N hydrochloric acid, 1 N sodium hydroxide and saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. addition50 ml of dichloromethane was added to the residue
  8. temperatureunder cooling with ice, and they
  9. stirringwere stirred for 30 minutes
  10. customwas elevated to room temperature
  11. stirringthe mixture was stirred for 15 hours
  12. customThe reaction liquid
  13. extractionAfter the extraction with dichloromethane
  14. washthe organic layer was successively washed with 1 N hydrochloric acid, 1 N sodium hydroxide and saturated aqueous NaCl solution
  15. dry with materialdried over anhydrous magnesium sulfate
  16. customThe solvent was evaporated under reduced pressure
  17. stirringwere stirred at 50° C. for 19 hours
  18. customThe reaction liquid
  19. extractionAfter the extraction with ethyl acetate
  20. washthe organic layer was successively washed with water and saturated aqueous NaCl solution
  21. customThe solvent was evaporated
  22. customthe residue was purified by the silica gel column chromatography

出典と根拠

ORDレコード
ord-3bea7c29b4ac438f9099cf797fe3ab35
出典データセット
uspto-grants-2008_07
特許番号
US07396844B1

反応ノート

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