Dichloromethane → HCID 86655960, compound

HRID 1486473Notes

Reaction equation

HRID 1486473 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH:20]1N=CN(C(N2C=NC=C2)=O)C=1.C(Cl)Cl.[NH2:35][C@H:36]([CH2:40][OH:41])[CH:37]([CH3:39])[CH3:38]>N1C=CC=CC=1>[CH2:2]([C:1]([NH:35][C@H:36]([CH2:40][OH:41])[CH:37]([CH3:39])[CH3:38])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:20]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 640993L-ValinolHCID 5284499Oleyl Alcohol

Product 1

HCID 86655960HCID 86655960, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To oleyl alcohol (22) (0.5 g, 1.58 mmol) in 5 ml pyridine, and while stirred at r.t., CDI (0.26 g, 1.58 mmol) was added. The reaction mixture was stirring at r.t for 48 hrs. Reaction was followed using TLC (100% DCM). When the starting material disappeared Valinol (0.162 g, 1.58 mmol) was added to the mixture was stirred for 1 week at room temperature. Reaction progress was followed by TLC (Eth. Ac100%). After the reaction was completed was the volatiles were removed under reduced pressure. The desired product Oleylcarbonyl-L-Valinol (25) was obtained using column chromatography (DCM/ethyl acetate.=1:1; v/v; I2).

Workup

  1. customReaction
  2. additionwas added to the mixture
  3. stirringwas stirred for 1 week at room temperature
  4. customReaction progress
  5. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-a5d4ec397ab1483099771c514c287dd0
Source dataset
uspto-grants-2016_08
Patent number
US09428448B2

Reaction notes

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