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Intermediates of (2S,4S,5S,7S)-5-amino-N-(2-carbamoyl-2,2-dimethylethyl)-4-hydroxy-7- {[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-8-methyl-(2-propan-2-yl)-nonanamide

IP.com Disclosure Number: IPCOM000204929D
Publication Date: 2011-Mar-13
Document File: 2 page(s) / 118K

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The IP.com Prior Art Database

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Intermediates of (2S,4S,5S,7S)-5-amino-N-(2-carbamoyl-2,2-dimethylethyl)-4-hydroxy-7- {[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-8-methyl-(2-propan-2-yl)-nonanamide

(2S,4S,5S,7S)-5-amino-N-(2-carbamoyl-2,2-dimethylethyl)-4-hydroxy-7- {[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-8-methyl-(2-propan-2-yl)-nonanamide hemifumarate having the following structure:

O

.

HO

OH

O

½

is indicated for treatment of hypertension, acting as a renin inhibitor.

Provided are processes for the preparation of its intermediates.

Example 1

Preparation of (2S,4S)-4-azido-2-isopropyl-4-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-1- (4-methoxy-3-(3-methoxypropoxy)phenyl)butyl isobutyrate

Ȉˇ˄˙˝

˄ ˛ ˚

Ȉˇ Ȉˇ ˄ ˄ ˄ Ȉ˙ ˝ Ȉˇ ˝ Ȉˇ ˝˄Ȉ˙ˇ ˝ ˛ ˄ ˄ ˝ ˚~ ˙ ˙Ȉ
(28.45 g, 0.06 mol) was dissolved in MeTHF (285 mL). Potassium carbonate (16.46 g, 0.12 mol), DMAP (1.02 g) and isobutyric anhydride (21.57 g, 0.14 mol) were added at 25 °C and the resulting mixture was stirred at 25 °C.

The mixture was quenched with water (250 mL), the organic layer was washed with brine (200 mLx2) and evaporated to give the desired compound as oil (29.62 g, yield 90.7 %).

Example 2


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