Lauric Acid → HCID 131728581, compound

HRID 2263559Notes

Reaction equation

HRID 2263559 reaction equation
[C:1]([OH:14])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([N:23]1[CH2:27][CH:26]([OH:28])[CH2:25][CH:24]1[CH:29]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[O:30][CH:31]([C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=1)[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)=[O:22].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>>[CH3:39][O:38][C:35]1[CH:36]=[CH:37][C:32]([CH:31]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[O:30][CH:29]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:24]2[CH2:25][CH:26]([OH:28])[CH2:27][N:23]2[C:21](=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15][C:1](=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:33][CH:34]=1

Participants

5

Reactant 4

HCID 3893Lauric 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 131728581HCID 131728581, compound

Procedure

Using the above procedure Dodecanoic acid (2.00 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 102b was isolated as a pale yellow solid (Yield, 5.2 g, 71%). 1H NMR (DMSO-d6, 400 MHz) δ=7.73-7.68 (m, 1H), 7.42-7.31 (m, 4H), 7.27-7.09 (m, 5H), 6.91-6.80 (m, 4H), 4.97 (d, J=3.90 Hz, 1H), 4.94 (d, J=3.90 Hz, 1H), 4.41-4.05 (m, 2H), 3.71 (s, 6H), 3.59-3.41 (m, 1H), 3.35-3.11 (m, 2H), 3.05-2.91 (m, 3H), 2.22-1.78 (m, 6H), 1.51-1.0 (m, 24H), 0.82 (t, J=6.34 Hz, 3H). 13C NMR (DMSO-d6, 400 MHz) δ=171.85, 170.93, 170.83, 158.10, 157.97, 145.09, 144.75, 135.87, 135.73, 135.47, 135.42, 129.60, 129.55, 127.85, 127.78, 127.57, 126.63, 126.53, 113.18, 113.09, 85.78, 85.11, 68.58, 67.45, 63.33, 55.60, 54.99, 54.96, 53.43, 38.21, 38.02, 36.30, 35.43, 34.17, 32.54, 31.31, 29.09, 29.03, 29.01, 28.97, 28.79, 28.74, 28.67, 26.19, 25.33, 24.55, 24.15, 22.10, 21.21, 13.94.

Workup

  1. customAfter work-up and column purification the pure amide 102b
  2. customwas isolated as a pale yellow solid (Yield, 5.2 g, 71%)

Sources & evidence

ORD record
ord-645940972b32428395a31fbeb3585f8b
Source dataset
uspto-grants-2010_12
Patent number
US07851615B2

Reaction notes

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