Hydrochloric Acid → 2(R,S)-Methyl-4(S)-hydroxy-5(S)-amino-7(S)-isopropyl-8-(p-tert-butyl-phenyl)-octanoic acid (N-butyl)amide hydrochloride

HRID 744770Notes

Reaction equation

[CH2:1]([NH:5][C:6](=[O:37])[CH:7]([CH3:36])[CH2:8][C@H:9]([OH:35])[C@@H:10]([NH:27]C(OC(C)(C)C)=O)[CH2:11][C@@H:12]([CH:24]([CH3:26])[CH3:25])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH3:4].[ClH:38]>O1CCOCC1>[ClH:38].[CH2:1]([NH:5][C:6](=[O:37])[CH:7]([CH3:36])[CH2:8][C@H:9]([OH:35])[C@@H:10]([NH2:27])[CH2:11][C@@H:12]([CH:24]([CH3:25])[CH3:26])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([CH3:21])([CH3:22])[CH3:23])=[CH:18][CH:19]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 20 °C

Procedure

111 mg of N-tert-butoxycarbonyl-2(R,S)-methyl-4(S)-hydroxy-5(S)-amino-7(S)-isopropyl-8-(p-tert-butyl-phenyl)-octanoic acid (N-butyl)amide are dissolved in 2 ml of 4N hydrochloric acid in dioxane at 0° C. and then stirred for 60 minutes at 20° C. The reaction mixture is concentrated by evaporation under reduced pressure and the residue is purified by means of FC (50 g of silica gel, dichloromethane/methanol=9:1). The title compound is obtained in the form of a diastereoisomeric mixture: Rf (dichloromethane/methanol=9:1)=0.20; Rt (I)=36.6 and 37.5 minutes; FAB-MS (M+H)+ =419.

Workup

concentrationThe reaction mixture is concentrated by evaporation under reduced pressure
customthe residue is purified by means of FC (50 g of silica gel, dichloromethane/methanol=9:1)

Sources & evidence

ORD record: ord-30d4c524dfc94522ba75c37630125872
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05559111

Reaction notes

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