Boc-D-phenylalanine → Methyl 5-[[5-bromo-4-(prop-2-ynyloxy)pyrimidin-2-yl]amino]-3-[[(2R)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxo-3-phenylpropyl]amino]benzoate

HRID 1785316노트

반응식

HRID 1785316 반응식
[C:1]([NH:8][C@@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH2:43][C:44]1[CH:45]=[C:46]([CH:51]=[C:52]([NH:54][C:55]2[N:60]=[C:59]([O:61][CH2:62][C:63]#[CH:64])[C:58]([Br:65])=[CH:57][N:56]=2)[CH:53]=1)[C:47]([O:49][CH3:50])=[O:48]>CN(C=O)C.C(OCC)(=O)C>[Br:65][C:58]1[C:59]([O:61][CH2:62][C:63]#[CH:64])=[N:60][C:55]([NH:54][C:52]2[CH:53]=[C:44]([NH:43][C:17](=[O:19])[C@H:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:45]=[C:46]([CH:51]=2)[C:47]([O:49][CH3:50])=[O:48])=[N:56][CH:57]=1

참가 물질

7

반응물 4

HCID 637610Boc-D-phenylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57593287Methyl 3-amino-5-[[5-bromo-4-(prop-2-ynyloxy)pyrimidin-2-yl]amino]benzoate

생성물 1

HCID 86760835Methyl 5-[[5-bromo-4-(prop-2-ynyloxy)pyrimidin-2-yl]amino]-3-[[(2R)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxo-3-phenylpropyl]amino]benzoate수율 83.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

N-BOC-D-phenylalanine (3.3 g), 1-hydroxy-1H-benzotriazole hydrate(1.9 g) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimid hydrochloride (2.37 g) were stirred in DMF (30 ml) for 30 minutes Then methyl 3-amino-5-[[5-bromo-4-(prop-2-ynyloxy)pyrimidin-2-yl]amino]benzoate (3.88 g) were added and the mixture stirred over night. Then ethyl acetate (500 ml) was added and the reaction mixture washed subsequently with hydrochloric acid (0.1 n), saturated NaHCO3-solution, water and brine. After drying (Na2SO4) the organic phase was evaporated and the residue subjected to column chromatography (ethyl acetate/dichloromethane) to yield 5.36 g of the title compound.

후처리

  1. washthe reaction mixture washed subsequently with hydrochloric acid (0.1 n), saturated NaHCO3-solution, water and brine
  2. dry with materialAfter drying (Na2SO4) the organic phase
  3. customwas evaporated

출처 및 근거

ORD 기록
ord-445f6cf854b840fb9be84fa43e1027e6
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504410B2

반응 노트

불러오는 중…