Bis-Aminoethylglycol → {2-[2-(2-Amino-ethoxy)-ethoxy]-ethyl}-carbamic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

HRID 1498003Notes

Reaction equation

HRID 1498003 reaction equation
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:31])[CH2:14][CH2:15][CH:16]3[C@@:21]4([CH3:30])[CH2:22][CH2:23][CH:24]([O:26][C:27](Cl)=[O:28])[CH2:25][C:20]4=[CH:19][CH2:18][CH:17]3[CH:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[CH2:32]([CH2:37][O:38][CH2:39][CH2:40][NH2:41])[O:33][CH2:34][CH2:35][NH2:36]>ClCCl>[CH3:1][C@@H:2]([C@@H:9]1[C@:13]2([CH3:31])[C@H:12]([C@H:17]3[C@H:16]([CH2:15][CH2:14]2)[C@:21]2([CH3:30])[C:20]([CH2:25][C@@H:24]([O:26][C:27](=[O:28])[NH:36][CH2:35][CH2:34][O:33][CH2:32][CH2:37][O:38][CH2:39][CH2:40][NH2:41])[CH2:23][CH2:22]2)=[CH:19][CH2:18]3)[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 70248Bis-AminoethylglycolHCID 54236888C28H45ClO2

Product 1

HCID 67367938{2-[2-(2-Amino-ethoxy)-ethoxy]-ethyl}-carbamic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of cholesteryl chloroformate (1 g, 2.23 mmol) in 25 mL dichloromethane was added dropwise under stirring to a solution of 2,2′-(ethylenedioxy)bis-(ethylamine) (495 mg, 3.34 mmol) in 75 mL dichloromethane. The reaction was stirred overnight at room temperature. The reaction was diluted with dichloromethane and extracted with water. The organic extract was dried over anhydrous MgSO4 dihydrate, filtered and evaporated. After purification on amino-modified silica gel (eluent: MeCl2->MeCl2/MeOH=975:25 v/v) the product (615 mg) was obtained as a white, waxy solid.

Workup

  1. extractionextracted with water
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous MgSO4 dihydrate
  4. filtrationfiltered
  5. customevaporated
  6. customAfter purification on amino-modified silica gel (eluent: MeCl2->MeCl2/MeOH=975:25 v/v) the product (615 mg)
  7. customwas obtained as a white, waxy solid

Sources & evidence

ORD record
ord-1657b45605ba4235b0b23bed70f03c38
Source dataset
uspto-grants-2015_12
Patent number
US09198947B2

Reaction notes

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