m-Chloroperbenzoic acid → HCID 178444620, 화합물

HRID 1396944노트

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HRID 1396944 반응식
[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

참가 물질

4

반응물 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

생성물 1

HCID 178444620HCID 178444620, 화합물수율 77.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-02a96f1e220347d798b97c82db4e5f0b
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901119B2

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