Methanol → Glyceryl 1,3-distearate

HRID 1259048ノート

反応式

HRID 1259048 の反応式
C1O[C:5]([OH:9])([CH2:7][OH:8])[CH2:4][O:3][C:2]1([OH:12])[CH2:10]O.[C:13]([OH:32])(=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].Cl.C(N=C=N[CH2:39][CH2:40][CH2:41]N(C)C)C.CO>CN(C)C1C=CN=CC=1.ClCCl.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[C:13]([O:8][CH2:7][CH:5]([CH2:4][O:3][C:2](=[O:12])[CH2:10][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:41][CH2:40][CH3:39])[OH:9])(=[O:32])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

参加物

9

反応物 4

HCID 887MethanolHCID 5281Stearic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4180364Dihydroxyacetone dimer

生成物 1

HCID 101269Glyceryl 1,3-distearate収率 33.6%

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

3.0 g of dihydroxyacetone dimer, 22.7 g of stearic acid, 16.8 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride salt, and 10.8 g of 4-dimethylaminopyridine were dissolved in 100 mL of dichloromethane, for overnight reaction under agitation at ambient temperature. Adding 0.5 L of methanol to the reaction solution, the generated powder was filtered and recovered. The powder recovered by filtration was washed with methanol. After the washed powder was dried, 6 g of the dried powder was dissolved in a mixture solution of 400 mL of tetrahydrofuran and 20 mL of aqueous 10% acetic acid solution, to which 1.1 g of sodium borohydride was added in small portions at 0° C. Subsequently, the resulting mixture was agitated at ambient temperature for 6 hours to promote the reaction. The resulting reaction solution was poured in saturated aqueous sodium hydrogen carbonate, for extraction in ethyl acetate. After the organic layer was dried, the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, to obtain 3.5 g of the intended product.

後処理

  1. customreaction under agitation at ambient temperature
  2. filtrationthe generated powder was filtered
  3. customrecovered
  4. filtrationThe powder recovered by filtration
  5. washwas washed with methanol
  6. customAfter the washed powder was dried
  7. dissolution6 g of the dried powder was dissolved in a mixture solution of 400 mL of tetrahydrofuran and 20 mL of aqueous 10% acetic acid solution, to which 1.1 g of sodium borohydride
  8. additionwas added in small portions at 0° C
  9. customthe reaction
  10. customThe resulting reaction solution
  11. customAfter the organic layer was dried
  12. concentrationthe organic layer was concentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-71d110c218a04a70bb1fd932f2cf64bd
出典データセット
uspto-grants-2013_06
特許番号
US08466255B2

反応ノート

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