tert-Butanol → Tert-butyl [5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]carbamate

HRID 1349476ノート

反応式

HRID 1349476 の反応式
[CH2:1]([O:8][C:9]1[C:10](=[O:35])[C:11](C(O)=O)=[CH:12][N:13]([CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29])[C:14]=1[C:15](=[O:25])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:38]([CH2:41]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:50])C=CC=CC=1.[Cl-].[NH4+].[C:62]([OH:66])([CH3:65])([CH3:64])[CH3:63]>CN(C)C=O.O>[CH2:1]([O:8][C:9]1[C:10](=[O:35])[C:11]([NH:38][C:41](=[O:50])[O:66][C:62]([CH3:65])([CH3:64])[CH3:63])=[CH:12][N:13]([CH2:26][CH:27]([O:30][CH3:31])[O:28][CH3:29])[C:14]=1[C:15](=[O:25])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 199401P,P-Diphenylphosphinic azideHCID 230776405-Benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid

生成物 1

HCID 58859159Tert-butyl [5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]carbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid (50 mg) in dimethylformamide (0.3 ml) were added triethylamine (0.07 ml) and diphenylphosphoryl azide (0.054 ml). After stirring at room temperature for 1 hr, tert-butanol (0.3 ml) was added, and the mixture was heated to 100° C. and stirred for 1 hr. After cooling to room temperature, saturated aqueous ammonium chloride solution (5 ml) and water (5 ml) were added, and the mixture was extracted twice with ethyl acetate (15 ml each). The ethyl acetate layer was washed with water, dried and concentrated. The obtained-residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to give tert-butyl [5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]carbamate (40 mg).

後処理

  1. temperaturethe mixture was heated to 100° C.
  2. stirringstirred for 1 hr
  3. temperatureAfter cooling to room temperature
  4. extractionthe mixture was extracted twice with ethyl acetate (15 ml each)
  5. washThe ethyl acetate layer was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe obtained-residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

出典と根拠

ORDレコード
ord-2bb20ac5e3de46e2bcae162915e8a216
出典データセット
uspto-grants-2007_05
特許番号
US07211572B2

反応ノート

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