Dicyclohexylcarbodiimide → HCID 71616257, compound

HRID 2204031Notes

Reaction equation

HRID 2204031 reaction equation
[N:1]1([CH:6]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:5]=[CH:4][N:3]=[CH:2]1.[Br-:26].O[CH2:28][CH2:29][CH2:30][P+:31]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br-:26].[N:1]1([CH:6]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:28][CH2:29][CH2:30][P+:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:19])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11025793(3-Hydroxypropyl)triphenylphosphonium bromideHCID 86691646HCID 86691646, compound

Product 1

HCID 71616257HCID 71616257, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 13-(1H-imidazol-1-yl)octadecanoic acid (365 mg, 1.041 mmol), (3-hydroxypropyl)triphenylphosphonium bromide (418 mg, 1.041 mmol) and DMAP (catalytic amount) in DCM (10 ml), was cooled to 0° C., to which was then added DCC (215 mg, 1.041 mmol) under N2 gas, and stirring continued overnight at room temperature. The reaction mixture was filtered and concentrated. The crude product was purified by silica gel column (5% MeOH in DCM) to give TPP-13-ISA as a gummy semi-solid (600 mg, 78%)

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe crude product was purified by silica gel column (5% MeOH in DCM)

Sources & evidence

ORD record
ord-c4ca6096c8114beba51bef0bb5b4443d
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

Loading…