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

HRID 841025ノート

反応式

HRID 841025 の反応式
[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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fc9e3dcbf02445a0a87632c9da3a574b
出典データセット
uspto-grants-2002_04
特許番号
US06369221B1

反応ノート

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