Methanol → Ethyl 4-(4-amino-3-phenylbutanamido)benzoate

HRID 2422942노트

반응식

HRID 2422942 반응식
[N+:1]([CH2:4][CH:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:6][C:7]([NH:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1)=[O:8])([O-])=O.CO>>[NH2:1][CH2:4][CH:5]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:6][C:7]([NH:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1)=[O:8]

참가 물질

3

반응물 2

HCID 887MethanolHCID 67242330Ethyl 4-(4-nitro-3-phenyl-butyrylamino)benzoate

생성물 1

HCID 67243563Ethyl 4-(4-amino-3-phenylbutanamido)benzoate

실험 절차

Ref. J. Org. Chem., 2000, 65, 8001. To a stirred solution of nitro compound 47 (0.749 g, 2.10 mmol) and NiCl2.6H2O (1.99 g, 8.40 mmol) in methanol (10 ml) NaBH4 (0.719 g, 18.93 mmol) was added portionwise over 20 min at 0° C. After stirring for 15 at room temperature, the solvent was removed under reduced pressure. Water (20 ml) and ethyl acetate (40 ml) were added to the solid residue. The resulting mixture was filtered through a celite bed which was washed with ethyl acetate (20 ml). After collecting the filtrate, the organic phase was separated, dried over Na2SO4 and the solvent removed under reduced pressure to afford amine 51 as an off white solid (0.596 g, 1.83 mmol, 87%). The amine was used in the next step without further purification.

후처리

  1. customthe solvent was removed under reduced pressure
  2. additionWater (20 ml) and ethyl acetate (40 ml) were added to the solid residue
  3. filtrationThe resulting mixture was filtered through a celite bed which
  4. washwas washed with ethyl acetate (20 ml)
  5. customAfter collecting the filtrate
  6. customthe organic phase was separated
  7. dry with materialdried over Na2SO4
  8. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-8545c269d1274ba1afb037607ca971e0
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960434B2

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