Pyridine → HCID 58472432, 화합물

HRID 547574노트

반응식

HRID 547574 반응식
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13][C@H:11]([OH:12])[CH2:10][C@H:2]1[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].N1C=CC=CC=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl>[S:33]([O:12][CH:11]1[CH2:13][N:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:2]([C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])[CH2:10]1)([C:30]1[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=1)(=[O:35])=[O:34]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 7408710Di-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

생성물 1

HCID 58472432HCID 58472432, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of Boc-Hyp-OtBu (0.5 g, 1.74 mmol) in DCM (20 mL) were added pyridine (0.550 g, 6.96 mmol) and p-toluenesulfonyl chloride (0.663 g, 3.48 mmol) at r.t. After being stirred at r.t. for 24 h, the reaction mixture was quenched with 1M HCl and extracted with DCM. The organic layer was successively washed with 1M HCl, water, brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by chromatography on silica gel and provided pure product, Cpd C (yellow solid). Spectral Data: 1H-NMR (CDCl3/400 MHz): 7.82 (d, J=8.3 Hz, 2H), 7.40 (d, J=8.3 Hz, 2H), 5.05 (m, 1H), 4.28 (m, 1H), 3.59 (m, 2H), 2.49 (s, 3H), 2.57 (m, 1H), 2.13 (m, 1H), 1.47 (s, 9H), 1.45 (s, 9H). MS (ES+, m/z): 442.2 (M++1, 30.0).

후처리

  1. customthe reaction mixture was quenched with 1M HCl
  2. extractionextracted with DCM
  3. washThe organic layer was successively washed with 1M HCl, water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromatography on silica gel
  7. customprovided pure product, Cpd C (yellow solid)

출처 및 근거

ORD 기록
ord-8c572b163f8642a68e02c0ae638f8466
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939546B2

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