1,4-Dioxane hydrochloride → L-norleucyl-L-proline amide hydrochloride

HRID 5336

Reaction equation

HRID 5336 reaction equation
C(OC([NH:8][C@H:9]([C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([NH2:20])=[O:19])=[O:15])[CH2:10][CH2:11][CH2:12][CH3:13])=O)(C)(C)C.[ClH:24].O1CCOCC1>>[ClH:24].[NH2:8][C@H:9]([C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([NH2:20])=[O:19])=[O:15])[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 53782269N-tert-butyloxycarbonyl-L-norleucyl-proline amide

Product 1

HCID 70082665L-norleucyl-L-proline amide hydrochloride

Procedure

The N-tert-butyloxycarbonyl-L-norleucyl-proline amide (1 g, 3.05 mmol) was placed in a round bottom flask to which freshly prepared 4N HCl/dioxane (25 ml) was added. The solution was stirred for 1 hour. Evaporation of solvent in vacuo and then crystallization of an oily residue from methanol/ethyl ether gave the title compound as a crystal-line product (0.76 g, 95%); oil, [α]D -17.7° (C=1; DMF); Rf 0.31 (1-butanol/acetic acid/water 4:1:1), Rf 0.42 (1 butanol/acetic acid/water, 4:1:5, upper phase).

Workup

  1. additionwas added
  2. customEvaporation of solvent in vacuo
  3. customcrystallization of an oily residue from methanol/ethyl ether

Sources & evidence

ORD record
ord-da46530a89434c3c8d249230d0da1142
Source dataset
uspto-grants-1993_09
Patent number
US05244884

Linked notes

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