Sodium Carbonate → (R)-5-[4-(2-Hydroxy-ethoxy)-phenyl]-3-[(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-methyl-propyl]-imidazolidine-2,4-dione

HRID 227154노트

반응식

HRID 227154 반응식
C(O[C:6]([NH:8][C@@H:9]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])(C)(C)C.IC1C=C(N)C(N)=CC=1.C(N(C(C)C)CC)(C)C.N1([O:43][C:44](N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[Na+].[Na+].C(OC(=O)[NH:63][C@H:64]([C:68](=O)[NH:69][C:70]1[CH:75]=[CH:74][C:73]([I:76])=[CH:72][C:71]=1[NH2:77])[CH:65]([CH3:67])[CH3:66])(C)(C)C.[C:80]([O:84][C:85](=O)N[C@H](C(=O)NC1C=C(I)C=CC=1N)C(C)C)([CH3:83])([CH3:82])C>CN(C)C=O>[OH:43][CH2:44][CH2:85][O:84][C:80]1[CH:82]=[CH:14][C:13]([C@H:9]2[NH:8][C:6](=[O:7])[N:63]([C@H:64]([C:68]3[NH:69][C:70]4[CH:75]=[CH:74][C:73]([I:76])=[CH:72][C:71]=4[N:77]=3)[CH:65]([CH3:66])[CH3:67])[C:10]2=[O:12])=[CH:15][CH:83]=1

참가 물질

9

반응물 7

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 83693Boc-L-ValineHCID 130500O-benzotriazol-1-yl-tetramethyluroniumHCID 112070494-Iodobenzene-1,2-diamineHCID 66815259[(S)-1-(2-amino-5-iodo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl esterHCID 66815284[(S)-1-(2-amino-4-iodo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester

생성물 1

HCID 178448265(R)-5-[4-(2-Hydroxy-ethoxy)-phenyl]-3-[(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-methyl-propyl]-imidazolidine-2,4-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To the solution of (S)-2-tert-butoxycarbonylamino-3-methyl-butyric acid (0.33 g, 1.5 mmol), 4-iodo-benzene-1,2-diamine (0.35 g, 1.5 mmol) and diisopropylethyl amine (0.8 mL, 4.5 mmol) in N,N-dimethylformamide (6 mL) was added dropwise a solution of O-benzotriazol-1-yl-N,N, N′,N′-tetramethyluronium hexaflurorophosphate (0.71 g, 1.75 mmol) N,N-dimethylformamide (2 mL). The reaction mixture was stirred for 12 hours at room temperature. After adding aqueous sodium carbonate solution, the reaction mixture was extracted with ethyl acetate and the organic layer was washed with aqueous sodium carbonate solution and brine, dried over sodium sulfate, filtered, and concentrated to give a mixture of regioisomers, [(S)-1-(2-amino-4-iodo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester and [(S)-1-(2-amino-5-iodo-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester (0.65 g, 100%).

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with aqueous sodium carbonate solution and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give

출처 및 근거

ORD 기록
ord-6a93aaf95e7e43888a36af294f31d324
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557221B2

반응 노트

불러오는 중…