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

HRID 1828412
ノート
印刷プレビュー

反応式

HRID 1828412 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6d35462f82eb462697301e392a270694
出典データセット
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07056917B2

反応ノート

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