Methanol → 20-(3-Hydrazino-3-oxopropyl)-2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro[5.1.11.2]heneicosane-21-one

HRID 1707309Notes

Reaction equation

HRID 1707309 reaction equation
C([O:13][C:14](=O)[CH2:15][CH2:16][N:17]1[C:30](=[O:31])[C:20]2([CH2:25][C:24]([CH3:27])([CH3:26])[NH:23][C:22]([CH3:29])([CH3:28])[CH2:21]2)[O:19][C:18]21[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)CCCCCCCCCCC.CO.[NH2:46][NH2:47]>C(OC)(C)(C)C.O1CCCC1.C(Cl)(Cl)Cl>[NH:46]([C:14](=[O:13])[CH2:15][CH2:16][N:17]1[C:30](=[O:31])[C:20]2([CH2:25][C:24]([CH3:27])([CH3:26])[NH:23][C:22]([CH3:28])([CH3:29])[CH2:21]2)[O:19][C:18]21[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)[NH2:47]

Participants

7

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 189631447-Oxa-3,20-diazadispiro[5.1.11.2]heneicosane-20-propanoic acid, 2,2,4,4-tetramethyl-21-oxo-, dodecyl ester

Product 1

HCID 1896313820-(3-Hydrazino-3-oxopropyl)-2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro[5.1.11.2]heneicosane-21-one

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

20-(3-Dodecyloxy-3-oxopropyl)-2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro[5.1.11.2]heneicosane-21-one (Sanduvor 3050™), 66.5 g (0.11 mole) was placed in a flask and dissolved with 150 ml methanol. To this was added 35 ml of hydrazine (54% in water) producing an immediate white precipitate. The mixture was stirred at ambient temperature for 28 hours. Most of the solvent was stripped using aspirator vacuum and the residue taken up in 100 ml methyl t-butyl ether and 175 ml tetrahydrofuran. The aqueous layer which separated was removed and the organic phase washed with three 50 ml portions of saturated sodium chloride. The organic material was dried with anhydrous magnesium sulfate, and the solvent was stripped using aspirator vacuum. The white semi-solid residue was slurried with pentane and isolated. The product weighed 39.4 g (79% of theory) and had two melting points at 171°-174° C. and 185° C. The infrared spectrum (in chloroform) showed a carbonyl band at 1680 cm-1.

Workup

  1. customproducing an immediate white precipitate
  2. customThe aqueous layer which separated
  3. customwas removed
  4. washthe organic phase washed with three 50 ml portions of saturated sodium chloride
  5. dry with materialThe organic material was dried with anhydrous magnesium sulfate
  6. customisolated
  7. customat 171°-174° C.
  8. custom185° C

Sources & evidence

ORD record
ord-b226f3283d964c49b08ed9a998d995f7
Source dataset
uspto-grants-1994_10
Patent number
US05352719

Reaction notes

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