1-Fluoro-2-nitrobenzene → (3S)-2-Oxo-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester

HRID 363867

反応式

HRID 363867 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N[C@@H:32](CN)[C:33]([OH:35])=[O:34])=O)(C)(C)C.F[C:39]1C=CC=CC=1[N+]([O-])=O.C([O-])(O)=O.[Na+]>O.CN(C=O)C>[CH3:39][O:35][C:33](=[O:34])[CH2:32][N:21]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][CH2:13][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:10]1=[O:12]

参加物

7

反応物 4

HCID 738951-Fluoro-2-nitrobenzeneHCID 516892Sodium BicarbonateHCID 2755946Boc-Dap-OHHCID 22881947N-[(1,1-Dimethylethoxy)carbonyl]-3-[(2-nitrophenyl)amino]-L-alanine

生成物 1

HCID 54305289(3S)-2-Oxo-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester収率 83%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

(2S)-2-tert-Butoxycarbonylamino-3-(2-nitrophenyl-amino)-propionic acid. (2S)-2-tert-Butoxycarbonylamino-3-aminopropionic acid (10 g, 49 mmol), 2-fluoronitrobenzene (5.7 ml, 54 mmol), and NaHCO3 (8.25 g, 98 mmol) was taken into 130 ml of DMF and heated at 80° C. for 18 h. The reaction was evaporated in vacuo to give a viscous orange residue that was dissolved in 300 ml of H2O and extracted with Et2O (3×150 ml). The aq. solution was acidified to pH 5 with 10% NaHSO4 and extracted with EtOAc (3×250 ml). The combined extracts were dried over anhydrous Na2SO4, filtered, and evaporated to give 12.64 g (83%) of the title compound as an orange amorphous solid: 1H NMR (CD3OD) δ 8.15-8.10 (1H,d), 7.54-7.48 (1H,t), 7.13-7.08 (1H, d), 6.73-6.65 (1H, t), 4.45-4.35 (1H, m), 3.9-3.8 (1H, dd), 3.65-3.55 (1H, dd), 1.45 (9H, s).

後処理

  1. customThe reaction was evaporated in vacuo
  2. customto give a viscous orange residue that
  3. extractionextracted with Et2O (3×150 ml)
  4. extractionextracted with EtOAc (3×250 ml)
  5. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-e1885b1e0ce445a9b243d4aaae4924df
出典データセット
uspto-grants-1999_02
特許番号
US05874424

関連ノート

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