Pyridine → HCID 58472432、化合物

HRID 547574ノート

反応式

HRID 547574 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 58472432HCID 58472432、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8c572b163f8642a68e02c0ae638f8466
出典データセット
uspto-grants-2011_05
特許番号
US07939546B2

反応ノート

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