Lithium Hydroxide → HCID 22729978, 화합물

HRID 2356129노트

반응식

HRID 2356129 반응식
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24]C)=O)=[CH:18][CH:17]=2)=[C:12]([O:26][CH3:27])[CH:11]=1)(C(C)(C)C)(C)C.[Li+].[OH-].[N+:30]([C:33]1[CH:34]=[C:35]([S:49]([NH2:52])(=[O:51])=[O:50])[CH:36]=[CH:37][C:38]=1[NH:39][CH2:40][CH2:41][S:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([O-:32])=[O:31].CCN=C=NCCCN(C)C>C1COCC1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([NH:52][S:49]([C:35]3[CH:36]=[CH:37][C:38]([NH:39][CH2:40][CH2:41][S:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[C:33]([N+:30]([O-:32])=[O:31])[CH:34]=3)(=[O:50])=[O:51])=[O:24])=[CH:20][CH:21]=2)=[C:12]([O:26][CH3:27])[CH:11]=1

참가 물질

8

반응물 4

HCID 3939Lithium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 8461424HCID 8461424, 화합물HCID 68454501HCID 68454501, 화합물

생성물 1

HCID 22729978HCID 22729978, 화합물

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of Example 438A (0.50 mmol) and 1M LiOH (0.60 mL) in THF (2 mL) was heated to 50° C., stirred for 3 hours, concentrated, dissolved in DMF (5 mL), and treated with a mixture of Example 77B (211 mg, 0.60 mmol), EDCI (193 mg, 1.0 mmol), and DMAP (50 mg). The mixture was stirred for 16 hours, treated with 1M HF (3 mL), stirred for 3 hours, diluted with ethyl acetate (100 mL), washed sequentially with 1M HCl (10 mL), water (20 mL), and brine (10 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50-100% ethyl acetate/hexanes to provide the desired product. MS (ESI(−)) m/e 592 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 8.79 (t, 1H), 8.62 (d, 1H), 7.92 (dd, 1H), 7.89 (d, 2H), 7.54 (d, 2H), 7.37 (m, 2H), 7.28 (r, 3H), 7.18 (tt, 1H), 7.06 (s, 1H), 6.97 (d, 1H), 4.54 (s, 2H), 3.76 (s, 3H), 3.66 (q, 2H), 3.20 (t, 2H).

후처리

  1. concentrationconcentrated
  2. dissolutiondissolved in DMF (5 mL)
  3. stirringThe mixture was stirred for 16 hours
  4. additiontreated with 1M HF (3 mL)
  5. stirringstirred for 3 hours
  6. washwashed sequentially with 1M HCl (10 mL), water (20 mL), and brine (10 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe concentrate was purified by flash column chromatography on silica gel with 50-100% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-3a8b377eccb349dcbe00d5360e86102f
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754886B2

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