Trifluoroacetic acid → HCID 12021270, 화합물

HRID 1058314노트

반응식

HRID 1058314 반응식
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

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 69939642HCID 69939642, 화합물

생성물 1

HCID 12021270HCID 12021270, 화합물수율 35.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ba27fb06bc4f42b2ad7d0fe18cf90ac3
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06515011B2

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