Acetic Acid → N-[(2S)-2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)propyl]-N-[2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)Propyl]amine

HRID 39372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 39372
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]([O:25][C:26]([NH:28][C@@H:29]([CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH:30]=O)=[O:27])([CH3:24])([CH3:23])[CH3:22].C([BH3-])#N.[Na+].C(O)(=O)C>C(O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:10][NH:11][CH2:30][CH:29]([NH:28][C:26]([O:25][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:27])[CH2:32][O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 11196731(S)-tert-butyl 3-(benzyloxy)-1-oxopropan-2-ylcarbamateHCID 60204732N2-Boc-(S)-3-(benzyloxy)propane-1,2-diamine

Produkt 1

HCID 66639988N-[(2S)-2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)propyl]-N-[2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)Propyl]amineAusbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The product from Example 17B (0.35 g, 1.25 mmol) and the product from Example 17A (0.36 g, 1.29 mmol) in absolute ethanol (12 mL) were treated with sodium cyanoborohydride (94 mg, 1.50 mmol) and a catalytic amount of acetic acid. The resulting mixture was stirred at ambient temperature overnight. The mixture was partitioned between water (40 mL) and ethyl acetate (3×40 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (hexanes:ethyl acetate, 1:1) to provide the title compound (0.15 g, 22%).

Aufarbeitung

  1. customThe mixture was partitioned between water (40 mL) and ethyl acetate (3×40 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5f4d3eb232c64b089e19cd6883476933
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524753B2

Notizen zur Reaktion

Wird geladen…