Palmitic Acid → HCID 131728583, compound

HRID 2263561Notes

Reaction equation

HRID 2263561 reaction equation
[C:1]([OH:18])(=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][CH3:16].[NH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([N:27]1[CH2:31][CH:30]([OH:32])[CH2:29][CH:28]1[CH:33]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[O:34][CH:35]([C:44]1[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=1)[C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)=[O:26].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH3:43][O:42][C:39]1[CH:40]=[CH:41][C:36]([CH:35]([C:44]2[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=2)[O:34][CH:33]([C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH:28]2[CH2:29][CH:30]([OH:32])[CH2:31][N:27]2[C:25](=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][NH:19][C:1](=[O:18])[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][CH3:16])=[CH:37][CH:38]=1

Participants

5

Reactant 4

HCID 985Palmitic AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1317282076-Amino-1-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexan-1-one

Product 1

HCID 131728583HCID 131728583, compound

Procedure

Using the above procedure Palmitic acid (2.57 g, 10 mmol) was coupled with the amine 100 (6.10 g, 11.45 mmol) using HBTU (4.54 g, 1.2 eq.) and DIEA (5 mL, 3.00 eq). After work-up and column purification the pure amide 102d was isolated as a white solid (Yield, 6.15 g, 79%). 1H NMR (DMSO-d6, 400 MHz) δ=7.74-7.66 (m, 1H), 7.37-7.22 (m, 4H), 7.21-7.12 (m, 5H), 6.87-6.79 (m, 4H), 4.98 (d, J=3.90 Hz, 1H), 4.90 (d, J=3.90 Hz, 1H), 4.40-4.07 (m, 2H), 3.71 (s, 6H), 3.59-3.42 (m, 1H), 3.34-3.13 (m, 2H), 3.02-2.87 (m, 3H), 2.20-1.80 (m, 6H), 1.46-1.08 (m, 32H), 0.82 (t, J=6.35 Hz, 3H). 13C NMR (DMSO-d6, 400 MHz) δ=171.84, 170.92, 170.81, 158.11, 157.98, 145.09, 144.74, 135.87, 135.72, 135.46, 135.41, 129.59, 129.55, 127.84, 127.74, 127.57, 126.55, 113.16, 113.07, 85.78, 85.12, 68.59, 67.45, 65.19, 63.33, 59.74, 55.61, 55.06, 54.95, 53.44, 44.58, 39.08, 38.87, 38.22, 38.02, 36.30, 35.44, 34.18, 32.54, 31.32, 29.09, 29.05, 29.00, 28.81, 28.74, 28.69, 26.20, 25.34, 24.55, 24.15, 22.12, 21.20, 14.06, 13.92.

Workup

  1. customAfter work-up and column purification the pure amide 102d
  2. customwas isolated as a white solid (Yield, 6.15 g, 79%)

Sources & evidence

ORD record
ord-695223ccc2ea418c8fe354a684386d9f
Source dataset
uspto-grants-2010_12
Patent number
US07851615B2

Reaction notes

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