Pyridine → HCID 23387526, compound

HRID 1170676Notes

Reaction equation

HRID 1170676 reaction equation
[Br:1][CH2:2][CH:3]([OH:23])[CH2:4][O:5][C:6](=[O:22])[C@H:7]([CH:19]([CH3:21])[CH3:20])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].N1C=CC=CC=1.[C:30](Cl)(=[O:48])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].C(=O)([O-])O.[Na+]>ClCCl>[Br:1][CH2:2][CH:3]([O:23][C:30](=[O:48])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:4][O:5][C:6](=[O:22])[C@H:7]([CH:19]([CH3:20])[CH3:21])[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8212Stearoyl chlorideHCID 516892Sodium BicarbonateHCID 23387525HCID 23387525, compound

Product 1

HCID 23387526HCID 23387526, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-bromo-2-hydroxy-1-(N-CBZ-L-valyloxy)-propane (7.9 g, 20 mmol) and pyridin (3.2 g, 40 mmol) in 250 ml dichloromethane was added dropwise a solution of stearoyl chloride (9.1 g, 30 mmol) in 50 ml dichloromethane between 10° C. and 15° C. The solution was stirred overnight at room temperature. 150 ml of 5% sodium hydrogen carbonate solution was added and the mixture stirred for 30 minutes. The organic phase was separated and the water phase was extracted two times with dichloromethane. The combined organic phases were dried with sodium sulfate and concentrated in vacuo. The product was isolated by silica gel column chromatography.

Workup

  1. stirringthe mixture stirred for 30 minutes
  2. customThe organic phase was separated
  3. extractionthe water phase was extracted two times with dichloromethane
  4. dry with materialThe combined organic phases were dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-6a65ed5795ad439a8bd8bf1bde94a2b2
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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