Methylhydrazine → HCID 21650354, compound

HRID 373888Notes

Reaction equation

HRID 373888 reaction equation
CNN.[Si:4]([O:11][CH2:12][CH:13]([O:24][N:25]1C(=O)C2=CC=CC=C2C1=O)[CH2:14][CH2:15][P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5]>ClCCl>[Si:4]([O:11][CH2:12][CH:13]([O:24][NH2:25])[CH2:14][CH2:15][P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])([C:7]([CH3:9])([CH3:8])[CH3:10])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 54196063HCID 54196063, compound

Product 1

HCID 21650354HCID 21650354, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methylhydrazine (0.97 ml, 18 mmol) was added to a solution of diethyl [4-(t-butyldimethylsilyloxy)-3-(phthalimidooxy)butyl]phosphonate (5.9 g, 12 mmol) in dichloromethane (40 ml). A white solid separated after a few minutes. The mixture was stirred overnight, filtered, the solvent evaporated and the residue chromatographed on silica gel using dichloromethane-methanol (98:2) as eluant. The title compound was obtained as a colorless oil (3.05 g, 70%). IR: υmax (film). 3320, 2970, 2940, 2860, 1595, 1470, 1390, 1250, 1160, 1060, 1030, 960, 840, 780, cm-1. 1H NMR: δH (CDCl3) 0.08 (6H, s, SiMe2), 0.9 (9H, s, SiBut), 1.3 (6H, t, J=7Hz, (OCH2CH3)2), 1.5-2.2 (4-H, m, CH2CH2P), 3.4-3.9 (3H, m, OCH2CH), 4.15 (4H, m, (OCH2CH3)2), 5.3 (2H, broad, D2O exchangeable NH2).

Workup

  1. customA white solid separated after a few minutes
  2. filtrationfiltered
  3. customthe solvent evaporated
  4. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-7d09e3166b6e4a0f8c3ac1d0ead62f76
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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