Stearic Acid → HCID 131728584, compound

HRID 2263562Notes

Reaction equation

HRID 2263562 reaction equation
[C:1]([OH:20])(=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][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][CH2:9][CH2:10][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 5281Stearic AcidHCID 1317282076-Amino-1-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexan-1-one

Product 1

HCID 131728584HCID 131728584, compoundYield 90%

Procedure

Using the above described procedure, stearic acid 101e (2.84 g, 10 mmol) was coupled with the amine 100 and after work-up and column purification the pure amide was isolated as a foam (7.17 g, 90%). 1H NMR (DMSO-d6, 400 MHz) δ=7.76-7.65 (m, 1H), 7.34-7.10 (m, 9H), 6.90-6.79 (m, 4H), 4.96 (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, 36H), 0.83 (t, J=6.1 Hz, 3H). 13C NMR (DMSO-d6, 400 MHz) δ=171.83, 170.92, 170.82, 162.29, 158.10, 157.97, 145.08, 144.74, 135.86, 135.42, 135.47, 129.59, 129.54, 127.84, 127.76, 127.57, 126.56, 113.18, 113.09, 85.78, 85.10, 68.57, 67.44, 65.19, 63.32, 54.97, 40.12, 38.21, 36.29, 35.77, 35.42, 34.16, 31.30, 30.75, 29.04, 28.78, 28.72, 28.65, 26.18, 25.33, 24.14, 22.10, 13.95.

Workup

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

Sources & evidence

ORD record
ord-af0ca5585a144d5195c2a173f3f3a6bb
Source dataset
uspto-grants-2010_12
Patent number
US07851615B2

Reaction notes

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