Diisopropylethylamine → HCID 86678328, compound

HRID 2407962Notes

Reaction equation

HRID 2407962 reaction equation
[CH2:1]([NH:11][C:12]([O:14][C@H:15]([CH2:41][O:42][C:43](=[O:55])[NH:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:16][S:17][CH2:18][C@H:19]([NH:23][C:24](=[O:40])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:20]([OH:22])=O)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].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.[NH2:89][CH2:90][CH2:91][O:92][CH2:93][CH2:94][O:95][CH2:96][CH2:97][O:98][CH2:99][CH2:100][P:101](=[O:108])([O:105][CH2:106][CH3:107])[O:102][CH2:103][CH3:104]>C(Cl)Cl>[CH2:106]([O:105][P:101]([CH2:100][CH2:99][O:98][CH2:97][CH2:96][O:95][CH2:94][CH2:93][O:92][CH2:91][CH2:90][NH:89][C:20](=[O:22])[C@@H:19]([NH:23][C:24](=[O:40])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:18][S:17][CH2:16][C@H:15]([O:14][C:12](=[O:13])[NH:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:41][O:42][C:43](=[O:55])[NH:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])(=[O:108])[O:102][CH2:103][CH3:104])[CH3:107]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86667767Diethyl 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethylphosphonateHCID 86678329HCID 86678329, compound

Product 1

HCID 86678328HCID 86678328, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-((R)-2,3-bis(decylcarbamoyloxy)propylthio)-2-palmitamidopropanoic acid and HBTU (1.2 eq) in DCM (0.06 M) was added DIEA (2.4 eq), followed by diethyl 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethylphosphonate (1.2 eq, from example 18, step 4). The reaction was stirred at room temperature for 4 hours. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using a gradient of 0-10% MeOH/DCM to afford the title compound as an off-white oil.

Workup

  1. customThe crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-12c65479580048c6b1ac1c2e6acbecc2
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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