Docosanoic Acid → HCID 131728587, compound

HRID 2263565Notes

Reaction equation

HRID 2263565 reaction equation
[C:1]([OH:24])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[NH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([N:33]1[CH2:37][CH:36]([OH:38])[CH2:35][CH:34]1[CH:39]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[O:40][CH:41]([C:50]1[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=1)[C:42]1[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=1)=[O:32]>>[CH3:49][O:48][C:45]1[CH:46]=[CH:47][C:42]([CH:41]([C:50]2[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=2)[O:40][CH:39]([C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[CH:34]2[CH2:35][CH:36]([OH:38])[CH2:37][N:33]2[C:31](=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][NH:25][C:1](=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:43][CH:44]=1

Participants

3

Reactant 2

HCID 8215Docosanoic AcidHCID 1317282076-Amino-1-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexan-1-one

Product 1

HCID 131728587HCID 131728587, compoundYield 41%

Procedure

Using the above described procedure, docosanoic acid 101h (3.41 g, 10 mmol) was coupled with the amine 100 and after work-up and column purification the pure amide was isolated as a foam (3.5 g, 41%). 1H NMR (DMSO-d6, 400 MHz) δ=7.69 (m, 1H), 7.32-6.80 (m, 13H), 4.98 (d, J=3.90 Hz, 0.7H), 4.88 (d, J=3.90 Hz, 0.3H), 4.40-4.05 (m, 2H), 3.71 (s, 6H), 3.59-3.42 (m, 1H), 3.34-3.13 (m, 2H), 3.10-2.87 (m, 3H), 2.20-1.80 (m, 6H), 1.50-1.08 (m, 44H), 0.81 (t, J=6.1 Hz, 3H). 13C NMR (DMSO-d6, 400 MHz) δ=171.78, 170.89, 170.79, 162.30, 162.25, 158.09, 157.97, 145.08, 144.73, 135.86, 135.70, 135.45, 135.40, 129.59, 129.53, 127.82, 127.72, 127.56, 126.69, 126.52, 113.14, 113.05, 85.78, 85.10, 68.58, 67.44, 65.19, 63.32, 55.60, 55.05, 54.96, 54.93, 38.22, 38.01, 36.30, 35.76, 35.43, 34.16, 32.53, 31.35, 30.74, 29.09, 28.87, 28.78, 28.73, 26.20, 25.35, 24.13, 22.13, 13.88.

Workup

  1. customafter work-up and column purification the pure amide

Sources & evidence

ORD record
ord-0f9125d0254d4a28801e6b5313ee9942
Source dataset
uspto-grants-2010_12
Patent number
US07851615B2

Reaction notes

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