Methanol → Glyceryl 1,3-distearate

HRID 1259048노트

반응식

HRID 1259048 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

HCID 101269Glyceryl 1,3-distearate수율 33.6%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-71d110c218a04a70bb1fd932f2cf64bd
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466255B2

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