Diisopropylethylamine → HCID 86300945, compound

HRID 1259001Notes

Reaction equation

HRID 1259001 reaction equation
[CH2:1]([C:19]([OH:62])([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]/[CH:52]=[CH:53]\[CH2:54]/[CH:55]=[CH:56]\[CH2:57][CH2:58][CH2:59][CH2:60]C)[CH:20]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:21][CH2:22]O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Cl.[CH3:64][N:65]([CH3:72])[CH2:66][CH2:67][CH2:68][C:69]([OH:71])=[O:70].CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>ClCCl.CN(C1C=CN=CC=1)C>[CH3:64][N:65]([CH3:72])[CH2:66][CH2:67][CH2:68][C:69]([O:71][CH2:22][CH2:21][CH:20]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:19]([OH:62])([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]/[CH:51]=[CH:52]\[CH2:53]/[CH:54]=[CH:55]\[CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:70]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 126916404-(Dimethylamino)butyric acid hydrochlorideHCID 86667528HCID 86667528, compound

Product 1

HCID 86300945HCID 86300945, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (14Z,17Z)-4-((9Z,12Z)-octadeca-9,12-dienyl)-3-((9Z,12Z)-octadeca-9,12-dienyloxy)tricosa-14,17-diene-1,4-diol (450 mg, 0.52 mmol), 4-(dimethylamino)butanoic acid hydrochloride (105 mg, 0.62 mmol), EDCI hydrochloride (120 mg, 0.62 mmol), DIPEA (225 μL, 1.3 mmol) in anhydrous dichloromethane (10 mL) was added DMAP (5 mg). The solution was stirred at room temperature under nitrogen for 64 hours. Upon completion, the solution was concentrated in vacuo to dryness and purified by column chromatography on silica gel 60 (eluted with 1:1 hexanes/Ethyl acetate) to afford (13Z,16Z)-4-hydroxy-4-((9Z,12Z)-octadeca-9,12-dienyl)-3-((9Z,12Z)-octadeca-9,12-dienyloxy)docosa-13,16-dienyl 4-(dimethylamino)butanoate as a colorless oil (375 mg, 75%). 1H NMR (400 MHz, CDCl3) δ 5.43-5.29 (m, 12H), 4.31-4.11 (m, 2H), 3.60-5.29 (m, 2H), 3.27-3.22 (m, 1H), 2.78 (t, 6H, J=6.4 Hz), 2.39-2.28 (m, 3H), 2.24 (s, 6H), 2.09-2.02 (m, 12H), 1.91-1.72 (m, 4H), 1.61-1.23 (m, 60H), 0.90 (t, 9H, J=7.0 Hz).

Workup

  1. concentrationUpon completion, the solution was concentrated in vacuo to dryness
  2. custompurified by column chromatography on silica gel 60 (eluted with 1:1 hexanes/Ethyl acetate)

Sources & evidence

ORD record
ord-ebb3e668369646f4aff67ee27901e624
Source dataset
uspto-grants-2013_06
Patent number
US08466122B2

Reaction notes

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