Diethyl Ether → (S)-Methyl 4-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate

HRID 660197노트

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HRID 660197 반응식
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.CN(C)[CH:56]=[O:57].C[CH2:60][O:61]CC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO>[C:1]([O:5][C:6]([NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([C:60]([O:57][CH3:56])=[O:61])=[CH:12][CH:11]=1)[CH3:9])=[O:17])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 5

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 56973617(S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamate

생성물 1

HCID 57432297(S)-Methyl 4-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate수율 94%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매

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온도
80 °C

실험 절차

A mixture of tert-butyl[(1S)-1-(4-bromophenyl)ethyl]carbamate (step 3, 14.73 g, 49.1 mmol), 1,3-bis(diphenylphosphino)-propane (2.03 g, 4.91 mmol), palladium (II) acetate (1.10 g, 4.91 mmol), triethylamine (20.5 mL, 147 mmol), N,N-dimethylforamide (120 mL) and methanol (180 mL) was stirred at 80° C. for 16 h under carbon monoxide atmosphere. After cooling to room temperature, the mixture was diluted with ether (800 mL) and washed with water (500 mL×3). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (5:1) to afford 12.83 g (94%) of the title compound as white solids:

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (500 mL×3)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified
  6. customby flush column chromatography on silica gel eluting with hexane/ethyl acetate (5:1)

출처 및 근거

ORD 기록
ord-74ed380daa874011a8c51b77913037c9
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084476B2

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