Triethylamine → 2-(t-Butyloxycarbonylamino)-4-(N-(Cbz-isoleucyl)amino)-1,5-diphenyl-3-hydroxypentane

HRID 847643

Reaktionsgleichung

Reaktionsgleichung von HRID 847643
[NH2:1][CH:2]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:3]([OH:20])[CH:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+](C1C=CC([O:37][C:38](=O)[C@H:39]([C@H:51]([CH2:53][CH3:54])[CH3:52])[NH:40][C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:42])=CC=1)([O-])=O.C(N(CC)CC)C>C1COCC1.[OH-].[Na+].C(Cl)(Cl)Cl.CO>[C:16]([O:15][C:13]([NH:12][CH:4]([CH:3]([OH:20])[CH:2]([NH:1][C:38](=[O:37])[C@H:39]([C@H:51]([CH2:53][CH3:54])[CH3:52])[NH:40][C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 2063382N-[(Phenylmethoxy)carbonyl]-L-isoleucine 4-nitrophenyl esterHCID 147043774-Amino-2-(t-butyloxycarbonylamino)-1,5-diphenyl-3-hydroxypentane

Produkt 1

HCID 228456432-(t-Butyloxycarbonylamino)-4-(N-(Cbz-isoleucyl)amino)-1,5-diphenyl-3-hydroxypentaneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittel2×HCID 6212ChloroformLösungsmittel4×HCID 8028TetrahydrofuranLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

The resultant compound of Example 11 (125 mg, 0.34 mmol), N-benzyloxycarbonyl-isoleucine p-nitrophenyl ester (196 mg, 0.51 mmol) and triethylamine (94 μL, 0.67 mmol) were combined with 1.0 mL of dry THF and stirred together at ambient temperature overnight. The reaction mixture was then heated at reflux temperature for 3 h. The cooled reaction mixture was then diluted with 5 mL of THF and 5 mL of 3M aqueous sodium hydroxide solution was added. The mixture was stirred at ambient temperature for approximately 0.5 h. and was then diluted with chloroform. The chloroform solution was washed with 3×25 mL of 0.5M aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue (227 mg) was taken up in approximately 5 mL of chloroform and applied to a 1.0×45 cm column of 40 mesh silica gel. The column was eluted @5-10 p.s.i. sequentially with 100 mL of chloroform, 100 mL of 0.5% methanol in chloroform and 100 mL of 1% methanol in chloroform to give 169 mg (81% yield) of the title compound; FAB MS M/Z: 618 (M+H)+. The 300 MHz 1NMR spectrum was consistent with the assigned structure. Analysis calculated for C36H47N3O6 : C, 69.99; H, 7.67; N, 6.80. Found: C, 69.26; H, 7.52; N, 6.61.

Aufarbeitung

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux temperature for 3 h
  3. customThe cooled reaction mixture
  4. additionwas added
  5. stirringThe mixture was stirred at ambient temperature for approximately 0.5 h.
  6. washThe chloroform solution was washed with 3×25 mL of 0.5M aqueous sodium hydroxide solution and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washThe column was eluted @5-10 p.s.i

Quellen und Nachweise

ORD-Eintrag
ord-654c606790264998895c6be050f5cfa7
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05142056

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