Lithium Hydroxide → HCID 22729978, Verbindung

HRID 2356129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356129
[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

Komponenten

8

Edukt 4

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

Produkt 1

HCID 22729978HCID 22729978, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3a8b377eccb349dcbe00d5360e86102f
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754886B2

Notizen zur Reaktion

Wird geladen…