Triethylamine → tert-butyl N-[1-(2,3-dichlorophenyl)-2-hydroxyethyl]carbamate

HRID 220692노트

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HRID 220692 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[Cl:20])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[BH4-].[Na+].C(=O)([O-])O.[Na+]>C1COCC1.O>[Cl:20][C:14]1[C:15]([Cl:19])=[CH:16][CH:17]=[CH:18][C:13]=1[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][OH:11]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 595367862-{[(Tert-butoxy)carbonyl]amino}-2-(2,3-dichlorophenyl)acetic acid

생성물 1

HCID 59536916tert-butyl N-[1-(2,3-dichlorophenyl)-2-hydroxyethyl]carbamate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Of the compound from Example 181A, 702 mg (2.19 mmol) were dissolved in 7 ml of THF under argon and cooled to 0° C. Then 306 μl (2.19 mmol) of triethylamine and 313 μl (2.41 mmol) of isobutyl chloroformate were added dropwise. The suspension was stirred at 0° C. for 1 h. It was filtered through a Seitz frit into a cooled flask, with washing with a little THF. The resulting filtrate was added slowly dropwise to a solution, cooled to 0° C., of 249 mg (6.58 mmol) of sodium borohydride in 1.5 ml of water. After 1 h, the batch was cautiously admixed with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic phase was also washed once with saturated aqueous sodium hydrogen carbonate solution and once with saturated aqueous sodium chloride solution. It was dried over sodium sulphate, filtered and freed from the solvent on a rotary evaporator. Drying in an HV gave 537 mg (56% of theory) of the title compound in 70% purity.

후처리

  1. filtrationIt was filtered through a Seitz frit into a cooled flask
  2. washwith washing with a little THF
  3. additionThe resulting filtrate was added slowly dropwise to a solution
  4. waitAfter 1 h
  5. extractionextracted with ethyl acetate
  6. washThe organic phase was also washed once with saturated aqueous sodium hydrogen carbonate solution and once with saturated aqueous sodium chloride solution
  7. dry with materialIt was dried over sodium sulphate
  8. filtrationfiltered
  9. customfreed from the solvent on a rotary evaporator
  10. customDrying in an HV

출처 및 근거

ORD 기록
ord-f212332e040c424b9156ba97e6aaafdb
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202895B2

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