Acetic acid, 2-chloro-, phenylmethyl ester → HCID 10283115, 화합물

HRID 2307738노트

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HRID 2307738 반응식
[C:1]([O:9][C@H:10]1[C@@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([O:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:14]([CH2:35][O:36][C:37](=[O:44])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:13][CH:11]1[OH:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C([O:58][C:59](=[O:62])[CH2:60]Cl)C1C=CC=CC=1.COC(C)(C)C>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[C:1]([O:9][C@H:10]1[C@@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([O:26][C:27](=[O:34])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C@@H:14]([CH2:35][O:36][C:37](=[O:44])[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[O:13][CH:11]1[O:12][CH2:60][C:59]([OH:62])=[O:58])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

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7

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HCID 8786Acetic acid, 2-chloro-, phenylmethyl esterHCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 111463962,3,4,6-Tetra-O-benzoylhexopyranose

생성물 1

HCID 10283115HCID 10283115, 화합물

시약·촉매·용매 2

HCID 70681Tetrabutylammonium Chloride촉매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

A mixture that consists of 59.66 g (100 mmol) of 2,3,4,6-tetra-O-benzoyl-mannopyranose, 1.39 g (5 mmol) of tetrabutylammonium chloride and 15.2 g (110 mmol) of anhydrous potassium carbonate in 500 ml of dimethylformamide is cooled to 0° C. At 0° C., 36.92 g (200 mmol) of chloroacetic acid benzyl ester is added in drops over 20 minutes while being stirred vigorously. It is stirred for one hour at 10° C. 250 ml of methyl-tert-butyl ether is added, the organic phase is separated, it is filtered and evaporated to the dry state in a vacuum. The residue is taken up in 500 ml of ethanol and mixed with 5 g of palladium (10%) on activated carbon. It is hydrogenated until hydrogen absorption is completed. Catalyst is filtered out, it is rewashed with a little ethanol, and the combined solutions are evaporated to the dry state in a vacuum. The residue is chromatographed on silica gel (mobile solvent: dichloromethane/n=hexane/ethanol/acetic acid=20:5:3:0.5). The product-containing fractions are concentrated by evaporation, dissolved in 400 ml of ethyl acetate and shaken out three times with 200 ml of water. Then, the organic phase is separated and evaporated to the dry state in a vacuum.

후처리

  1. stirringIt is stirred for one hour at 10° C
  2. customthe organic phase is separated
  3. filtrationit is filtered
  4. customevaporated to the dry state in a vacuum
  5. additionmixed with 5 g of palladium (10%) on activated carbon
  6. customIt is hydrogenated until hydrogen absorption
  7. filtrationCatalyst is filtered out
  8. customthe combined solutions are evaporated to the dry state in a vacuum
  9. customThe residue is chromatographed on silica gel (mobile solvent: dichloromethane/n=hexane/ethanol/acetic acid=20:5:3:0.5)
  10. concentrationThe product-containing fractions are concentrated by evaporation
  11. dissolutiondissolved in 400 ml of ethyl acetate
  12. stirringshaken out three times with 200 ml of water
  13. customThen, the organic phase is separated
  14. customevaporated to the dry state in a vacuum

출처 및 근거

ORD 기록
ord-42947a17a1344963a0cf2418a8343509
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06831164B2

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