Diisobutylaluminum hydride → HCID 22860091, 화합물

HRID 1720437

반응식

HRID 1720437 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[S:13][C:12]([C:14]#[C:15][C@H:16]([N:18]([OH:22])[C:19]([NH2:21])=[O:20])[CH3:17])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[S:13][C:12](/[CH:14]=[CH:15]/[C@H:16]([N:18]([OH:22])[C:19]([NH2:21])=[O:20])[CH3:17])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 14487Diisobutylaluminum hydrideHCID 3086671Atreleuton

생성물 1

HCID 22860091HCID 22860091, 화합물수율 20%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (R)-N-{3-[5-(4-fluorophenylmethyl)thien-2-yl]-1-methyl-2-propynyl}-N-hydroxyurea (0.316g, 1.05 mmol), prepared as in Example 1, step 4, in THF (8 mL) at -70° C. was added DIBAL (5.23 mL, 5.25 mmol). The reaction was slowly allowed to warm to ambient temperature over 17 hours. The reaction was quenched into an aqueous 1M H3PO4 solution and extracted with ethyl acetate. The combined organic layers were washed with aqueous NaHCO3, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica gel (50% ethyl acetate/hexanes/1% acetic acid). The resulting solid was crystallized from hot ethyl acetate/hexanes to yield 0.063 g (20% ) of E-N-[3-(5-(4-Fluorophenylmethyl)-thien-2-yl)-1-(R)-methyl-2-propenyl]-N-hydroxyurea. m.p. 143°-4° C). MS (DCI/NH3) m/e 321 (M+H)+, 338 (M+NH4)+. 1H NMR (DMSO-d6, 300 MHz) δ1.17(d, J=7.2 Hz, 3H), 4.08 (s, 2H), 4.73 (m, 1H), 5.88 (dd, J=6.3, 15.6 Hz, 1H), 6.33 (s, 2H), 6.55 (d, J=15.6 Hz, 1H), 6.77 (d, J=4.2 Hz, 1H), 6.83 (d, J=4.2 Hz, 1H), 7.12 (m, 2H), 7.29 (m, 2H), 9.02 (s, 1H). Anal Calcd for C17H17FN2O2S: C, 59.98; H, 5.35; N, 8.74. Found C, 60.15; H, 5.11; N, 8.75.

후처리

  1. customThe reaction was quenched into an aqueous 1M H3PO4 solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with aqueous NaHCO3
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel (50% ethyl acetate/hexanes/1% acetic acid)
  7. customThe resulting solid was crystallized from hot ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-1ec20c48c35943dfb53959b8ca8a902f
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05506261

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