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

HRID 1349476노트

반응식

HRID 1349476 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2bb20ac5e3de46e2bcae162915e8a216
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211572B2

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