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 227154ノート

反応式

HRID 227154 の反応式
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

参加物

9

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6a93aaf95e7e43888a36af294f31d324
出典データセット
uspto-grants-2009_07
特許番号
US07557221B2

反応ノート

読み込み中…