Ethanol → tert-butyl N-[2-amino-1-(4-chlorophenyl)ethyl]carbamate

HRID 423087노트

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HRID 423087 반응식
CS(O[CH2:6][CH:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)(=O)=O.[N-:23]=[N+]=[N-].[Na+].C(O)C>CN(C=O)C.[Pd]>[NH2:23][CH2:6][CH:7]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1

참가 물질

6

반응물 3

HCID 702EthanolHCID 33557Sodium AzideHCID 577502782-(Tert-butoxycarbonylamino)-2-(4-chlorophenyl)ethyl methanesulfonate2회

생성물 1

HCID 57750386tert-butyl N-[2-amino-1-(4-chlorophenyl)ethyl]carbamate수율 99%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A solution of 2-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)ethyl methanesulfonate (Intermediate 23) (535 mg, 1.53 mmol) in DMF (8 mL) was treated with sodium azide (199 mg, 3.06 mmol) and the mixture was heated at 80° C. for 1 hour. The mixture was cooled and allowed to stir at room temperature overnight. The solution was partitioned between ethyl acetate and water. The organic layer was washed twice with water then dried with magnesium sulfate, filtered and concentrated until the final volume was approximately 5 mL. Ethanol (20 mL) and 10% palladium on carbon (75 mg, 0.07 mmol) were added. The resulting suspension was stirred under an atmosphere of hydrogen at ambient pressure and temperature for 1 hour. The mixture was filtered and the filtrate was concentrated under reduced pressure to give tert-butyl 2-amino-1-(4-chlorophenyl)ethylcarbamate as a gum (410 mg, 99%).

후처리

  1. temperatureThe mixture was cooled
  2. customThe solution was partitioned between ethyl acetate and water
  3. washThe organic layer was washed twice with water
  4. dry with materialthen dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated until the final volume
  7. stirringThe resulting suspension was stirred under an atmosphere of hydrogen at ambient pressure and temperature for 1 hour
  8. filtrationThe mixture was filtered
  9. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-32c5a0e8da454e40985b831be5d49397
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101623B2

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