Myristic Acid → HCID 131728582, compound

HRID 2263560Notes

Reaction equation

HRID 2263560 reaction equation
[C:1]([OH:16])(=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][CH3:14].[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([N:25]1[CH2:29][CH:28]([OH:30])[CH2:27][CH:26]1[CH:31]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[O:32][CH:33]([C:42]1[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=1)[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)=[O:24].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>>[CH3:41][O:40][C:37]1[CH:38]=[CH:39][C:34]([CH:33]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=2)[O:32][CH:31]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH:26]2[CH2:27][CH:28]([OH:30])[CH2:29][N:25]2[C:23](=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:17][C:1](=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:35][CH:36]=1

Participants

5

Reactant 4

HCID 11005Myristic 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 131728582HCID 131728582, compound

Procedure

Using the above procedure Myristic acid (2.30 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 102c was isolated as a pale yellow solid (Yield, 6.10 g, 80%). 1H NMR (DMSO-d6, 400 MHz) δ=7.72-7.65 (m, 1H), 7.35-7.26 (m, 4H), 7.27-7.12 (m, 5H), 6.90-6.80 (m, 4H), 4.99 (d, J=3.91 Hz, 1H), 4.89 (d, J=3.91 Hz, 1H), 4.41-4.10 (m, 2H), 3.71 (s, 6H), 3.57-3.42 (m, 1H), 3.37-3.11 (m, 2H), 3.05-2.91 (m, 3H), 2.25-1.80 (m, 6H), 1.52-1.08 (m, 28H), 0.83 (t, J=6.34 Hz, 3H). 13C NMR (DMSO-d6, 400 MHz) δ=171.84, 170.93, 170.82, 158.11, 157.98, 145.09, 144.75, 135.87, 135.72, 135.47, 135.42, 129.60, 129.55, 127.84, 127.75, 127.72, 126.56, 113.17, 113.08, 85.78, 85.12, 68.58, 67.45, 65.19, 63.33, 55.61, 55.06, 54.99, 53.44, 39.08, 38.87, 38.22, 38.02, 36.31, 35.44, 34.18, 32.54, 31.32, 29.09, 29.04, 28.99, 28.80, 28.74, 28.64, 26.20, 25.34, 24.55, 24.15, 22.11, 13.93.

Workup

  1. customAfter work-up and column purification the pure amide 102c
  2. customwas isolated as a pale yellow solid (Yield, 6.10 g, 80%)

Sources & evidence

ORD record
ord-fce5bf75d0c944dab64464daf908dd02
Source dataset
uspto-grants-2010_12
Patent number
US07851615B2

Reaction notes

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