1-Phenethylamine, (+)- → 3-((2-Amino-2-methyl-3-phenylpropoxy)methyl)-5-(1-cyanocyclopentyl)-N-((R)-1-phenylethyl)benzamide

HRID 899480Notes

Reaction equation

HRID 899480 reaction equation
C(OC([NH:8][C:9]([CH3:36])([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:10][O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([C:22]2([C:27]#[N:28])[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:21]=1)[C:16]([OH:18])=O)=O)(C)(C)C.[C:37]1([C@H:43]([NH2:45])[CH3:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[NH2:8][C:9]([CH3:36])([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:10][O:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([C:22]2([C:27]#[N:28])[CH2:23][CH2:24][CH2:25][CH2:26]2)[CH:21]=1)[C:16]([NH:45][C@@H:43]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH3:44])=[O:18]

Participants

3

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 673191833-((2-Tert-butoxycarbonylamino-2-methyl-3-phenylpropoxy)methyl)-5-(1-cyanocyclopentyl)benzoic acid

Product 1

HCID 117523093-((2-Amino-2-methyl-3-phenylpropoxy)methyl)-5-(1-cyanocyclopentyl)-N-((R)-1-phenylethyl)benzamide

Procedure

Prepared from 3-((2-tert-butoxycarbonylamino-2-methyl-3-phenylpropoxy)methyl)-5-(1-cyanocyclopentyl)benzoic acid and (R)-1-phenylethanamine using a similar procedure as described for the preparation of Example 20. HRMS ES calculated for C32H37N3O2: 496.2959, found: 496.2958.

Workup

  1. customas described for the preparation of Example 20

Sources & evidence

ORD record
ord-354ac556fe9a4cf983615e17abbd976c
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

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