Sodium hydride → N-(tert-Butoxycarbonyl)-N-(3,6,9-trioxadecyl)-O-benzylhydroxylamine

HRID 2380435Notes

Reaction equation

HRID 2380435 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].S(C1C=CC(C)=CC=1)(O[CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])(=O)=O>CN(C=O)C>[C:3]([O:7][C:8]([N:10]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 736159Tert-butyl N-(benzyloxy)carbamateHCID 99488982-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

Product 1

HCID 15101734N-(tert-Butoxycarbonyl)-N-(3,6,9-trioxadecyl)-O-benzylhydroxylamineYield 77.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
72 °C

Procedure

N-(tert-Butoxycarbonyl)-N-(3,6,9-trioxadecyl)-O-benzylhydroxylamine (14 ) was synthesized by adding sodium hydride (80% oil dispersion, 0.488 g, 16.3 mmol) to N-(tert-butoxycarbonyl)-O-benzylhydroxylamine [Ramasamy, supra] (2.66 g, 11.9 mmol) in dry DMF (20 mL), and stirring was continued for several minutes. 3,6,9-Trioxadecyl tosylate [Schultz et al, supra] (4.93 g, 15.5 mmol) in DMF (3 mL) was added by syringe, and the suspension was heated at 72° C. for 18 hours under nitrogen. After cooling, the reaction was quenched with water (100 mL) and then extracted with ether (4×50 mL). The combined organic layers were washed with brine (100 mL) and the solvent was removed in vacuo. Column chromatography with 4% EtOH/CHCl3 produced 3.40 g (77%) of (14) as a liquid: NMR δ 1.50 (s, 9 H), 3.31 (s, 3 H), 3.5-3.7 (m, 12 H), 4.82 (s, 2 H), 7.25-7.41 (m, 5 H), Analysis: (C19H31NO6) C, H, N.

Workup

  1. customN-(tert-Butoxycarbonyl)-N-(3,6,9-trioxadecyl)-O-benzylhydroxylamine (14 ) was synthesized
  2. waitwas continued for several minutes
  3. temperatureAfter cooling
  4. customthe reaction was quenched with water (100 mL)
  5. extractionextracted with ether (4×50 mL)
  6. washThe combined organic layers were washed with brine (100 mL)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1d5ae47c76e34dfbb9a9692e7abd99be
Source dataset
uspto-grants-1994_11
Patent number
US05367113

Reaction notes

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