Lithium Hydroxide → HCID 22729978、化合物

HRID 2356129ノート

反応式

HRID 2356129 の反応式
[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

参加物

8

反応物 4

HCID 3939Lithium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 8461424HCID 8461424、化合物HCID 68454501HCID 68454501、化合物

生成物 1

HCID 22729978HCID 22729978、化合物

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3a8b377eccb349dcbe00d5360e86102f
出典データセット
uspto-grants-2010_07
特許番号
US07754886B2

反応ノート

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