Water → HCID 21193346, compound

HRID 443242Notes

Reaction equation

HRID 443242 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][OH:11].[CH2:20](Br)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].O>CN(C=O)C>[CH2:33]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][OH:11])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 8208Myristyl bromideHCID 21193412HCID 21193412, compound

Product 1

HCID 21193346HCID 21193346, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the alcohol from Step A (218 mg, 0.82 mmol), tetradecyl bromide (170 μL, 0.9 mmol) and CsCO3 (532 mg, 1.63 mmol) in DMF (8 mL) was stirred for 16 hs at room temperature under argon. The mixture was poured into water and extracted with EtOAc. The organic extracts were combined, washed with water and brine, dried (MgSO4), and concentrated in vacuo to give an oil. Purification by chromatography (SiO2, 20% EtOAc in hexanes) gave the title compound as a solid.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customPurification by chromatography (SiO2, 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f6d8b976bba640f5ab8039dfbb2da5d4
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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