N-Benzylphenethylamine → 9-(Benzyl-phenethyl-amino)-nonanoic acid

HRID 1799665Notes

Reaction equation

HRID 1799665 reaction equation
COC(=O)CCCCCCCC=O.C(NCCC1C=CC=CC=1)C1C=CC=CC=1.C[O:31][C:32](=[O:57])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][N:41]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[CH2:50]([N:41]([CH2:42][CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][C:32]([OH:57])=[O:31])[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

4

Reactant 3

HCID 65055N-BenzylphenethylamineHCID 74732Methyl 9-oxononanoateHCID 668749379-(Benzyl-phenethyl-amino)-nonanoic acid methyl ester

Product 1

HCID 668747569-(Benzyl-phenethyl-amino)-nonanoic acid

Procedure

The title compound, m/e=406.6 ([M+H]+), was produced in analogy with example 64, steps 1 to 4. Thus, 9-oxononanoic acid methyl ester was reacted in step 1 with N-benzyl-2-phenylethylamine, leading to 9-(benzyl-phenethyl-amino)-nonanoic acid methyl ester, which was hydrolyzed in step 2 to afford 9-(benzyl-phenethyl-amino)-nonanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride, leading to (R)-3-[9-(benzyl-phenethyl-amino)-nonanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-7cf964bd03014e8fbe78b0dfd9b2b219
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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