Benzylamine → N-benzyl-2-tert-butoxy-carbonylamino-5-trifluoromethoxybenzamide

HRID 841025노트

반응식

HRID 841025 반응식
[CH2:1]([NH:8][C:9](=[O:29])[C:10]1[CH:15]=[C:14]([O:16][C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:12][C:11]=1NC(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=[N:38][CH:39]2CCCCC2)CCCCC1.[C:45]([O:49]C(NC1C=CC(OC(F)(F)F)=CC=1C(O)=O)=O)([CH3:48])([CH3:47])[CH3:46].[OH:67]N1C2C=CC=CC=2N=N1.C(N)C1C=CC=CC=1>O1CCCC1.C(OCC)(=O)C.CCCCC>[CH2:1]([NH:8][C:9](=[O:29])[C:10]1[CH:15]=[C:14]([O:16][C:17]([F:18])([F:19])[F:20])[CH:13]=[C:12]([N:38]=[C:39]=[O:67])[C:11]=1[O:49][C:45]([CH3:48])([CH3:47])[CH3:46])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

9

반응물 5

HCID 7504BenzylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 27734412-((tert-Butoxycarbonyl)amino)-5-(trifluoromethoxy)benzoic acidHCID 22620722N-Benzyl-2-tert-butoxycarbonylamino-5-trifluoromethoxybenzamide

생성물 1

HCID 86757935N-benzyl-2-tert-butoxy-carbonylamino-5-trifluoromethoxybenzamide

시약·촉매·용매 3

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

N-Benzyl-2-tert-butoxycarbonylamino-5-trifluoromethoxybenzamide may be prepared in the following manner: 12.9 g of N,N′-dicyclohexylcarbodiimide are added to a solution, kept under an argon atmosphere at −10° C., of 20 g of 2-tert-butoxycarbonylamino-5-trifluoromethoxybenzoic acid, 16.9 g of 1-hydroxybenzotriazole and 6.8 g of benzylamine in 400 ml of anhydrous tetrahydrofuran. The mixture is stirred for 2 hours at the same temperature and then for 16 hours at a temperature close to 20° C. After cooling to 0° C., the insoluble matter is separated by filtration, washed with ethyl acetate and the filtrate is concentrated to dryness under reduced pressure (2 kPa). The product obtained is dissolved in 60 ml of ethyl acetate and the solution is washed twice with 25 ml of a saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2 kPa). The product obtained is resuspended in a mixture of petroleum ether and pentane (50-50 by volume), separated by filtration, washed with the mixture of petroleum ether and pentane and dried under reduced pressure (2 kPa). 21.7 g of N-benzyl-2-tert-butoxy-carbonylamino-5-trifluoromethoxybenzamide are thus obtained in the form of a cream-coloured solid melting at 144° C.

후처리

  1. customfor 16 hours at a temperature close to 20° C
  2. customthe insoluble matter is separated by filtration
  3. washwashed with ethyl acetate
  4. concentrationthe filtrate is concentrated to dryness under reduced pressure (2 kPa)
  5. customThe product obtained
  6. washthe solution is washed twice with 25 ml of a saturated aqueous sodium hydrogen carbonate solution
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated to dryness under reduced pressure (2 kPa)
  9. customThe product obtained
  10. customseparated by filtration
  11. washwashed with the mixture of petroleum ether and pentane
  12. customdried under reduced pressure (2 kPa)

출처 및 근거

ORD 기록
ord-fc9e3dcbf02445a0a87632c9da3a574b
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369221B1

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