m-Chloroperbenzoic acid → HCID 178444620、化合物

HRID 1396944ノート

反応式

HRID 1396944 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C@@H:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[N:12]2[C:26](=[O:45])[C@@H:27]([CH2:33][N:34]([CH:43]=[O:44])[O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:10])=[N:6][CH:7]=1.ClC1C=C(C(OO)=[O:54])C=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C@@H:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[N:12]2[C:26](=[O:45])[C@@H:27]([CH2:33][N:34]([CH:43]=[O:44])[O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:10])=[N+:6]([O-:54])[CH:7]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 86706376phenylmethyl (3S)-3-{[(5-fluoro-2-pyridinyl)amino]carbonyl}-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl) heptanoyl]-1-pyrazolidinecarboxylate

生成物 1

HCID 178444620HCID 178444620、化合物収率 77.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of phenylmethyl (3S)-3-{[(5-fluoro-2-pyridinyl)amino]carbonyl}-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-1-pyrazolidinecarboxylate (130 mg, 0.210 mmol) in dichloromethane (DCM) (4 mL) under nitrogen at 0° C. was added 3-chlorobenzenecarboperoxoic acid (141 mg, 0.629 mmol) in one portion. The reaction mixture was stirred at 0° C. for 10 min, then warmed up to room temperature and stirred overnight. The reaction was quenched by addition of sat. aq. NaHCO3 and extracted with DCM twice. The combined organic extracts were dried over Na2SO4, filtered and concentrated to afford the crude product as a white semi-solid. The crude product was purified by RP-HPLC to provide phenylmethyl (3S)-3-{[(5-fluoro-1-oxido-2-pyridinyl)amino]carbonyl}-2-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-1-pyrazolidinecarboxylate (103 mg, 77%). LCMS: (M+H)+: 636.0.

後処理

  1. temperaturewarmed up to room temperature
  2. stirringstirred overnight
  3. customThe reaction was quenched by addition of sat. aq. NaHCO3
  4. extractionextracted with DCM twice
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford the crude product as a white semi-solid
  9. customThe crude product was purified by RP-HPLC

出典と根拠

ORDレコード
ord-02a96f1e220347d798b97c82db4e5f0b
出典データセット
uspto-grants-2014_12
特許番号
US08901119B2

反応ノート

読み込み中…