Dimethylformamide → N-tert-butyloxycarbonyl-[(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine

HRID 2923

반응식

HRID 2923 반응식
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN(C)C=O.Cl.[CH3:46][O:47][C:48]1[CH:54]=[C:53]([CH3:55])[CH:52]=[C:51]([O:56][CH3:57])[C:49]=1[NH2:50]>C(OC(C)C)(C)C.C(OCC)(=O)C.C(N(CC)CC)C>[C:4]([O:3][C:1]([NH:8][CH2:9][C:10](=[O:12])[NH:50][C:49]1[C:51]([O:56][CH3:57])=[CH:52][C:53]([CH3:55])=[CH:54][C:48]=1[O:47][CH3:46])=[O:2])([CH3:5])([CH3:6])[CH3:7]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 189364892,6-Dimethoxy-4-methylaniline hydrochloride

생성물 1

HCID 18936465N-tert-butyloxycarbonyl-[(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine수율 96%

시약·촉매·용매 3

HCID 7914Diisopropyl Ether용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

6.6 g of N-Boc-glycine and 15.6 g of BOP are successively added to 100 ml of dimethylformamide and then, at 0° C., 14 ml of triethylamine are added dropwise. The mixture is left for 20 minutes at 0° C. and 6.7 g of 2,6-dimethoxy-4-methylaniline hydrochloride are then added portionwise. The reaction mixture is left at room temperature for 15 hours. 400 ml of ethyl acetate are added to the reaction mixture and the organic phase is successively washed with 3×200 ml of water, with a 1N aqueous sodium hydroxide solution and then with water. The organic phase is dried over anhydrous sodium sulphate. Evaporation of the solvent leaves a semi-crystalline residue which is solidified in diisopropyl ether to provide N-tert-butyloxycarbonyl-[(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine, in the form of white crystals; M.p.=146° C.; Yield: 96%.

후처리

  1. waitThe reaction mixture is left at room temperature for 15 hours
  2. washthe organic phase is successively washed with 3×200 ml of water, with a 1N aqueous sodium hydroxide solution
  3. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  4. customEvaporation of the solvent
  5. customleaves a semi-crystalline residue which

출처 및 근거

ORD 기록
ord-9cb77feee68640b1aefc6e6668171bff
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731340

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