Diisopropylethylamine → Propylene Glycol Dilaurate

HRID 2407860Notes

Reaction equation

HRID 2407860 reaction equation
[C:1]([O:14][C@H:15]([CH2:41][O:42][C:43](=[O:55])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:16]SC[C@@H](C(O)=O)NC(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.NCCC1C=NC=CC=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:43]([O:42][CH2:41][CH:15]([O:14][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH3:16])(=[O:55])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67414703(5R,9R)-9-(dodecanoyloxy)-1-(9H-fluoren-9-yl)-3,12-dioxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylic acid

Product 1

HCID 90838Propylene Glycol Dilaurate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (5R,9R)-9-(dodecanoyloxy)-1-(9H-fluoren-9-yl)-3,12-dioxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylic acid (6, 1 eq) and HBTU (1.2 eq) were stirred in dry DCM (0.1 M) at room temperature. 3-(2-aminoethyl)pyridine (1.2 eq) was then added followed by diisopropylethylamine (2.0 eq) and the reaction was allowed to stir at room temperature for 2 hours. The crude reaction mixture was then loaded directly onto a silica column and purified by purified by flash chromatography on a COMBIFLASH® system (ISCO) using a 100% Hex, 0-50% EtOAc/Hex, 100% EtOAc gradient to give (R)-3-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-oxo-3-(2-pyridin-3-yl)ethylamino) propylthio)propane-1,2-diyl didodecanoate.

Workup

  1. customThe crude reaction mixture
  2. custompurified
  3. customby purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-9be6c9e175ff475abe8ab932b51d65ac
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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