1,1'-Carbonyldiimidazole → (5-Benzyloxycarbonylamino-6-hydroxy-hexyl)-carbamic acid tert-butyl ester

HRID 1026528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026528
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[BH4-].[Na+].[H][H]>C1COCC1.O>[C:24]([O:23][C:21](=[O:22])[NH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH2:13][OH:14])([CH3:27])([CH3:25])[CH3:26]

Komponenten

7

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 294900N6-Boc-N2-Cbz-DL-lysineHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 14498533(5-Benzyloxycarbonylamino-6-hydroxy-hexyl)-carbamic acid tert-butyl esterAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 2-benzyloxycarbonylamino-6-tert-butoxycarbonylamino-hexanoic acid (Cbz-Lys(Boc)-OH) (Chem-Impex International, 3.8 g, 10 mmol) in THF (25 mL) in a 100 mL round flask was added 1,1′-carbonyldiimidazole (CDI) (1.7 g, 10.5 mmol) at room temperature. After 20 minutes, the THF solution was transferred via a Teflon canula (φ=2 mm) to a stirred solution of sodium borohydride (0.75 g, 20 mmol) in water (10 mL) in a 1 L round flask immersed in a water bath at 5-10° C. The addition caused a strong evolution of hydrogen gas and the mixture was stirred for a couple of hours. The volatiles were then removed on a rotovap, and the residue was dissolved in ethyl acetate (150 mL). The ethyl acetate solution was extracted successively with cold 1 N HCl (2×50 mL), saturated sodium bicarbonate solution (2×50 mL), brine (100 mL), and was dried with anhydrous sodium sulfate. The dried ethyl acetate solution was then pass through a one inch flash pad of silica gel, and concentrated to provide a colorless solid (3.3 g, 91%), TLC Rf=0.24 (95:5:2 EtOAc:MeOH:H2O).

Aufarbeitung

  1. customimmersed in a water bath at 5-10° C
  2. additionThe addition
  3. customThe volatiles were then removed on a rotovap
  4. dissolutionthe residue was dissolved in ethyl acetate (150 mL)
  5. extractionThe ethyl acetate solution was extracted successively with cold 1 N HCl (2×50 mL), saturated sodium bicarbonate solution (2×50 mL), brine (100 mL)
  6. dry with materialwas dried with anhydrous sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-63f6af641c264c22a1969b41cd190fcd
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729258B2

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