Sodium hydride → 1-tert-butoxycarbonyl-2(S)-(2-(1-propoxy)ethyl)-4-(1-naphthoyl)piperazine

HRID 1598460Notes

Reaction equation

HRID 1598460 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:10][C@@H:9]1[CH2:26][CH2:27][OH:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:31](I)[CH2:32][CH3:33]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:10][C@@H:9]1[CH2:26][CH2:27][O:28][CH2:31][CH2:32][CH3:33])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 129668321-tert-Butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-naphthoylpiperazine

Product 1

HCID 228841241-tert-butoxycarbonyl-2(S)-(2-(1-propoxy)ethyl)-4-(1-naphthoyl)piperazine

Procedure

The product from Step B was reacted with sodium hydride (0.220 g, 60% dispersion in oil, 5.4 mmol) and n-propyl iodide (0.375 mL, 3.85 mmol) according to the procedure described in Example 7, Step C. The crude product was chromatographed on silica gel with 30% ethyl acetate in hexane. The title compound was obtained as a foam, (0.400 g).

Workup

  1. customThe crude product was chromatographed on silica gel with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2d3bcb8457f74da8bc6e70e6e8595b84
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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