Sodium triacetoxyborohydride → HCID 54338209, Verbindung

HRID 1780805

Reaktionsgleichung

Reaktionsgleichung von HRID 1780805
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[CH3:15])=[O:6].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:33]([O:37][C:38]([NH:40][C@H:41]([CH:63]=O)[CH2:42][S:43][C:44]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:39])([CH3:36])([CH3:35])[CH3:34]>ClCCCl>[C:33]([O:37][C:38]([NH:40][C@@H:41]([CH2:42][S:43][C:44]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[CH2:63][NH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[CH3:15])=[O:6])=[O:39])([CH3:34])([CH3:35])[CH3:36]

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 64565863-amino-N-(2,3-dimethylphenyl)benzamideHCID 10388929N-Boc-S-trityl-(L)-cysteinal

Produkt 1

HCID 54338209HCID 54338209, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 2 (0.28 g) in 12 mL of 1,2-dichloroethane at 0° C. was added sodium triacetoxyborohydride (0.36 g) and N-t-butyloxycarbonyl-S-(triphenyl- methyl)cysteinal (0.35 g). The cooling bath was removed and the mixture was stirred for 4 h at 20° C. The solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was extracted with 50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a foam. NMR (300 MHz, CDCl3) δ 8.17 (1H, b), 7.46-7.18 (15H, m), 6.60 (1H, m), 3.13(2H, m,), 2.45(3H, m), 2.30 (3H, s), 2.18 (3H, s), 1.42 (9H, s).

Aufarbeitung

  1. customThe cooling bath was removed
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe ethyl acetate layer was extracted with 50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-62f6a466590c4ce697af1f2b5e7f422b
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05631280

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