Trifluoroacetic acid → HCID 12021270、化合物

HRID 1058314ノート

反応式

HRID 1058314 の反応式
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:31][N:32]2[CH2:35][CH:34]([OH:36])[CH2:33]2)=[C:13]([CH:30]=1)[CH2:14][NH:15][C:16](=[O:29])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1C(OC(C)(C)C)=O>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:31][N:32]2[CH2:35][CH:34]([OH:36])[CH2:33]2)=[C:13]([CH:30]=1)[CH2:14][NH:15][C:16](=[O:29])[C@@H:17]1[CH2:21][CH2:20][CH2:19][NH:18]1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 69939642HCID 69939642、化合物

生成物 1

HCID 12021270HCID 12021270、化合物収率 35.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

TFA (3 mL) was added to a stirred solution of N-{5-chloro-2-[(3-hydroxyazetidin-1-yl)methyl]benzyl}-1-(tert-butoxycarbonyl)-L-prolinamide (210 mg, 0.49 mmol) in CH2Cl2 (6 mL) at 0° C. After 90 min the solution was concentrated and the residue was partitioned between CH2Cl2 and 10% NaHCO3. The aqueous layer was saturated with NaCl and then extracted with more CH2Cl2. The combined organic layers were washed with brine, dried over (Na2SO4) and then evaporated. The reside was purified by chromatography on silica (ammonia saturated CHCl3/MeOH, 93:7) to give N-{5-chloro-2-[(3-hydroxyazetidin-1-yl)methyl]benzyl}-L-prolinamide (55.8 mg) as a glass: 1H NMR (CDCl3, 400 MHz) δ 1.71 (m, 2H), 1.93 (m, 1H), 2.16 (m, 1H), 2.92 (m, 2H), 3.05 (m, 2H), 3.39 (m, 2H), 3.61 (dd, J=12.3, 20.7 Hz, 2H), 3.72 (dd, J=6.4, 8.6 Hz, 2H), 4.28-4.46 (m, 3H), 7.12 (d, J=8.1 Hz), 7.19 (dd, J=2.2, 8.1 Hz), 7.36 (d, J=2.0 Hz, 1H), 9.09 (br s, 1H).

後処理

  1. concentrationAfter 90 min the solution was concentrated
  2. customthe residue was partitioned between CH2Cl2 and 10% NaHCO3
  3. extractionextracted with more CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over (Na2SO4)
  6. customevaporated
  7. customThe reside was purified by chromatography on silica (ammonia saturated CHCl3/MeOH, 93:7)

出典と根拠

ORDレコード
ord-ba27fb06bc4f42b2ad7d0fe18cf90ac3
出典データセット
uspto-grants-2003_02
特許番号
US06515011B2

反応ノート

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