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Trifluoroacetic acid → 2-[(Phenylmethyl)oxy]-N-3-pyridinyl-5-{[(2R)-2-pyrrolidinylmethyl]oxy}benzamide

HRID 1623785
ノート
印刷プレビュー

反応式

HRID 1623785 の反応式
FC(F)(F)C(O)=O.[C:8]1([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@H:24]3[CH2:28][CH2:27][CH2:26][N:25]3C(OC(C)(C)C)=O)=[CH:18][C:17]=2[C:36]([NH:38][C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[O:37])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O-])(O)=O.[Na+]>ClCCl>[C:8]1([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@H:24]3[CH2:28][CH2:27][CH2:26][NH:25]3)=[CH:18][C:17]=2[C:36]([NH:38][C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[O:37])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 866682001,1-Dimethylethyl (2R)-2-[({4-[(phenylmethyl)oxy]-3-[(3-pyridinylamino)carbonyl]phenyl}oxy)methyl]-1-pyrrolidinecarboxylate

生成物 1

HCID 699366462-[(Phenylmethyl)oxy]-N-3-pyridinyl-5-{[(2R)-2-pyrrolidinylmethyl]oxy}benzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

反応条件

温度
25 °C

実験手順

Trifluoroacetic acid (1.5 ml, 19.47 mmol) was added dropwise to an ice-cooled solution of 1,1-dimethylethyl (2R)-2-[({4-[(phenylmethyl)oxy]-3-[(3-pyridinylamino)carbonyl]phenyl}oxy)methyl]-1-pyrrolidinecarboxylate (may be prepared as described in Description 73; 500 mg, 0.99 mmol) in dichloromethane (15 ml). After stirring at 25° C. for 2 h, the pH of the solution was adjusted to 7-8 by adding aqueous NaHCO3 solution. The mixture was extracted with dichloromethane. The dichloromethane layer was washed with brine, dried over Na2SO4, and concentrated to obtain a crude product. Half of the crude product was purified by pre-HPLC (Gilson GX-281, waters X-Bridge 5 μm, 100*19 mm; A: 0.04% NH3.H2O/water, B: CH3CN; 0-7 min, 35%-50%; 7-14 min, 95%; RT=6.5 min) to yield the title compound as a light yellow solid. 70 mg.

後処理

  1. extractionThe mixture was extracted with dichloromethane
  2. washThe dichloromethane layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto obtain a crude product
  6. customHalf of the crude product was purified by pre-HPLC (Gilson GX-281, waters X-Bridge 5 μm, 100*19 mm
  7. custom0-7 min, 35%-50%
  8. custom7-14 min, 95%

出典と根拠

ORDレコード
ord-4963f6137c2a4ac4b865ea375ebb1e15
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08778939B2

反応ノート

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