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1,2-Dichloroethane → N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-1-[(2R)-2-hydroxy-2-phenylethanoyl]-L-prolinamide

HRID 857758
ノート
印刷プレビュー

反応式

HRID 857758 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:17]2[CH:21]=[N:20][N:19]=[N:18]2)=[C:6]([CH:16]=1)[CH2:7][NH:8][C:9](=[O:15])[C@@H:10]1[CH2:14][CH2:13][CH2:12][NH:11]1.[CH:22]1[CH:27]=[C:26]2N=NN(O)[C:25]2=[CH:24][CH:23]=1.[OH2:32].[CH2:33](Cl)[CH2:34]Cl.C(N(C(C)C)CC)(C)C.CN(C=[O:50])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:17]2[CH:21]=[N:20][N:19]=[N:18]2)=[C:6]([CH:16]=1)[CH2:7][NH:8][C:9](=[O:15])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:33](=[O:50])[C@H:34]([OH:32])[C:26]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 69655818N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide

生成物 1

HCID 58760139N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-1-[(2R)-2-hydroxy-2-phenylethanoyl]-L-prolinamide

実験手順

To a solution of R-mandelic acid (60 mg, 0.39 mmol), N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (Example 26, Step B, 120 mg, 0.39 mmol, HPLC RT=2.25 min, method A), and HOBt hydrate (60 mg, 0.39 mmol) in DMF (3 mL) was added EDC (98 mg, 0.51 mmol). Diisopropylethylamine was then added slowly in portions (˜0.05 mL total) to bring the pH of the solution to 6–7 as measured on wetted E. Merck pH indicator strips. The mixture was stirred at ambient temperature for 18 h, and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (10 mL). The EtOAc layer was separated, dried over anhydrous MgSO4, and filtered. The filtrate solvent was removed under reduced pressure and the residue was purified by pressurized silica gel column chromatography using EtOAc as eluant. Product-containing fractions were combined and the solvent was removed under reduced pressure to give the title compound as an amorphous solid (TLC Rf=0.6 (EtOAc); HPLC RT=2.82 min, method A; LCMS m/z=441).

後処理

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between EtOAc (50 mL) and saturated aqueous NaHCO3 (10 mL)
  3. customThe EtOAc layer was separated
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate solvent was removed under reduced pressure
  7. customthe residue was purified by pressurized silica gel column chromatography
  8. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-af0357fa4f2549acbc445f07925b96da
出典データセット
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07144899B2

反応ノート

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