1-(2-Aminoethyl)piperidin-4-ol → 5(S)-Tert-butoxycarbonylamino-4(S)-hydroxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid N-[2-(4-hydroxypiperidin-1-yl)-ethyl]-amide

HRID 2256734Notes

Reaction equation

HRID 2256734 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH:30]1[CH2:34][C@@H:33]([CH3:35])[C:32](=[O:36])[O:31]1)[CH2:10][C@@H:11]([CH:27]([CH3:29])[CH3:28])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:37][CH2:38][CH2:39][N:40]1[CH2:45][CH2:44][CH:43]([OH:46])[CH2:42][CH2:41]1>>[OH:46][CH:43]1[CH2:44][CH2:45][N:40]([CH2:39][CH2:38][NH:37][C:32](=[O:36])[C@H:33]([CH3:35])[CH2:34][C@H:30]([OH:31])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:10][C@@H:11]([CH:27]([CH3:29])[CH3:28])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])[CH:14]=2)[CH2:41][CH2:42]1

Participants

3

Reactant 2

HCID 27564251-(2-Aminoethyl)piperidin-4-olHCID 228657322-{1 (S)-tert-butoxycarbonylamino-3(S)-isopropyl-4-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-butyl}-4(R)-methyl-tetrahydrofuran-5-one

Product 1

HCID 542953995(S)-Tert-butoxycarbonylamino-4(S)-hydroxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid N-[2-(4-hydroxypiperidin-1-yl)-ethyl]-amide

Procedure

102 mg of 2-{1(S)-tert-butoxycarbonylamino-3(S)-isopropyl-4-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-butyl}-4(R)-methyl-tetrahydrofuran-5-one (Example 105e) and 0.5 g of N-(2-aminoethyl)-4-hydroxypiperidine are stirred for 2 hours at 80° C. The reaction mixture is purified by means of FC (60 g of silica gel, dichloromethane/methanol=4:1). The title compound is obtained: Rf (dichloromethane/methanol=4:1)=0.16.

Workup

  1. customThe reaction mixture is purified by means of FC (60 g of silica gel, dichloromethane/methanol=4:1)

Sources & evidence

ORD record
ord-a29935392aef4939b7160220bad68500
Source dataset
uspto-grants-1997_08
Patent number
US05654445

Reaction notes

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