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Ammonia → tert-Butyl N-[4-(3-amino-3-oxopropyl)-2-pyridyl]carbamate

HRID 1828412
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HRID 1828412 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([OH:19])=O)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:22](CC)CC)C.ClC(OCC)=O.N>O1CCCC1>[NH2:22][C:17](=[O:19])[CH2:16][CH2:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:14]=1
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참가 물질

6

반응물 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 220637293-{2-[(tert-Butoxycarbonyl)amino]-4-pyridyl)propanoic acid

생성물 1

HCID 22063511tert-Butyl N-[4-(3-amino-3-oxopropyl)-2-pyridyl]carbamate수율 106%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

3-{2-[(tert-Butoxycarbonyl)amino]-4-pyridyl}propanoic acid (11.16 g, 41.92 mmol) dissolved in tetrahydrofuran (200 ml) was added with triethylamine (9 ml, 62.89 mmol), cooled with ice, and then added dropwise with ethyl chloroformate (6 ml, 62.89 mmol). The reaction mixture was stirred for 10 minutes, and then added with aqueous ammonia (50 ml) dissolved in tetrahydrofuran (50 ml) at 0° C. The reaction mixture was stirred for 20 minutes under ice cooling, and then the solvent was evaporated under reduced pressure. The resulting residue was washed with water and extracted with chloroform. The resulting organic layer was washed with saturated brine, and the organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 11.794 g (100%) of the title compound as brown crystals without purification.

후처리

  1. temperaturecooled with ice
  2. stirringThe reaction mixture was stirred for 20 minutes under ice cooling
  3. customthe solvent was evaporated under reduced pressure
  4. washThe resulting residue was washed with water
  5. extractionextracted with chloroform
  6. washThe resulting organic layer was washed with saturated brine
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6d35462f82eb462697301e392a270694
출처 데이터셋
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07056917B2

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