Oleic Acid → HCID 131728585, compound

HRID 2263563Notes

Reaction equation

HRID 2263563 reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]1[CH2:33][CH:32]([OH:34])[CH2:31][CH:30]1[CH:35]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[O:36][CH:37]([C:46]1[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=1)[C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)=[O:28]>>[CH3:45][O:44][C:41]1[CH:42]=[CH:43][C:38]([CH:37]([C:46]2[CH:51]=[CH:50][C:49]([O:52][CH3:53])=[CH:48][CH:47]=2)[O:36][CH:35]([C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)[CH:30]2[CH2:31][CH:32]([OH:34])[CH2:33][N:29]2[C:27](=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][NH:21][C:1](=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:39][CH:40]=1

Participants

3

Reactant 2

HCID 445639Oleic AcidHCID 1317282076-Amino-1-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexan-1-one

Product 1

HCID 131728585HCID 131728585, compoundYield 98%

Procedure

Using the above described procedure, oleic acid 101f (2.83 g, 10 mmol) was coupled with the amine 100 and after work-up and column purification the pure amide was isolated as aa oil (7.7 g, 98%). 1H NMR (DMSO-d6, 400 MHz) δ 7.71-7.67 (m, 1H), 7.34-7.10 (m, 9H), 6.90-6.79 (m, 4H), 5.33-5.26 (m, 2H), 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), 3.34-3.20 (m, 2H), 3.18-3.10 (m, 1H), 3.02-2.92 (m, 3H), 2.20-1.80 (m, 6H), 1.50-1.04 (m, 39H), 0.83 (t, J=6.1 Hz, 3H). 13C NMR (DMSO-d6, 400 MHz) δ=171.81, 170.92, 170.83, 158.09, 157.96, 145.08, 144.74, 135.87, 135.72, 135.42, 129.61, 129.54, 127.86, 127.74, 127.57, 126.56, 113.18, 113.09, 85.78, 85.10, 68.57, 67.44, 65.19, 63.32, 54.97, 54.92, 48.59, 45.71, 40.12, 38.21, 38.02, 36.29, 35.41, 34.16, 32.53, 31.28, 29.09, 28.84, 28.69, 28.66, 28.59, 28.55, 26.58, 26.56, 26.19, 25.32, 24.54, 24.14, 22.10, 13.94.

Workup

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

Sources & evidence

ORD record
ord-7ea45b7ea83841eca48a684a5a04e5ed
Source dataset
uspto-grants-2010_12
Patent number
US07851615B2

Reaction notes

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