Sodium Hydroxide → 2,5-Di-(N-(Cbz-isoleucinyl)amino)-3,4dihydroxy-1,6-diphenylhexane

HRID 1078130

Reaktionsgleichung

Reaktionsgleichung von HRID 1078130
[NH2:1][C@H:2]([C@@H:10]([OH:22])[C@H:11]([OH:21])[C@@H:12]([NH2:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+](C1C=CC(O[C:33](=[O:50])[C@H:34]([C@H:46]([CH2:48][CH3:49])[CH3:47])[NH:35][C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:37])=CC=1)([O-])=O.[OH-:51].[Na+]>O1CCCC1>[C:36]([NH:35][C@H:34]([C:33]([NH:1][CH:2]([CH:10]([OH:22])[CH:11]([OH:21])[CH:12]([NH:20][C:33](=[O:50])[C@H:34]([C@H:46]([CH2:48][CH3:49])[CH3:47])[NH:35][C:36]([O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:50])[C@H:46]([CH2:48][CH3:49])[CH3:47])([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:51]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 2063382N-[(Phenylmethoxy)carbonyl]-L-isoleucine 4-nitrophenyl esterHCID 10990240(2S,3R,4R,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane

Produkt 1

HCID 228455822,5-Di-(N-(Cbz-isoleucinyl)amino)-3,4dihydroxy-1,6-diphenylhexaneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 10 mg (0.033 mmol) of the resultant compound of Example 171 and 38.6 mg (0.10 mmol) of Cbz-isoleucine p-nitrophenyl ester in 0.2 ml of tetrahydrofuran was stirred at ambient temperature for 21 h. The resulting misture was diluted with 1 ml of tetrahydrofuran, treated with 0.5 ml of 3N NaOH, stirred for 45 min, extracted with chloroform, washed sequentially with 3N NaOH and saturated brine, dried over MgSO4, and concentrated. The residue was purified on silica gel by eluting with 2% methanol in chloroform to provide 23 mg (86%) of the desired compound. Mass spectrum: (M+H)+ =795.

Aufarbeitung

  1. stirringstirred for 45 min
  2. extractionextracted with chloroform
  3. washwashed sequentially with 3N NaOH and saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel
  7. washby eluting with 2% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-dab3ee642ec246688805674ab5838dcf
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05545750

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