Sodium hydride → HCID 117642809, compound

HRID 1507754Notes

Reaction equation

HRID 1507754 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]([CH3:14])([CH3:13])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].CS(O[CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH3:41])(=O)=O>CN(C=O)C>[CH3:13][C:5]([CH3:14])([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:4][O:3][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH3:41]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21930814m-PEG7-MsHCID 54272639Tert-butyl 3-hydroxy-2,2-dimethylpropanoate

Product 1

HCID 117642809HCID 117642809, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% wt in oil) (400 mg, 10 mmol) was added to a stirred solution of tert-butyl 3-hydroxy-2,2-dimethylpropanoate (57) (1.74 g, 10 mmol) in DMF (20 mL) at 0° C., after 30 min a solution of 2,5,8,11,14,17,20-heptaoxadocosan-22-yl methanesulfonate (2.79 g, 6.67 mmol) in DMF (10 mL) was added dropwise, and the reaction mixture was allowed to warm to RT and stirred for 16 h. The reaction was quenched with water (100 mL) and the aqueous layer was extracted with DCM (2×100 mL), the combined organic layers were washed with brine (3×100 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (120 g, 0-10% MeOH in EtOAc) to afford tert-butyl 25,25-dimethyl-2,5,8,11,14,17,20,23-octaoxahexacosan-26-oate (58) (1.59 g, 48%) as a colourless oil: 1H NMR (400 MHz, CDCl3) δ: 3.65-3.51 (m, 32H), 3.40 (s, 2H), 3.36 (s, 3H), 1.41 (s, 9H), 1.11 (s, 6H).

Workup

  1. additionwas added dropwise
  2. customThe reaction was quenched with water (100 mL)
  3. extractionthe aqueous layer was extracted with DCM (2×100 mL)
  4. washthe combined organic layers were washed with brine (3×100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography (120 g, 0-10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-9880b79475f4415bb167a8ec6b6fe8e2
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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