Tetrahydrofuran → Boc-Ser(Bzl)-Asn-OH

HRID 22455

반응식

HRID 22455 반응식
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].O.C1COCC1.C(N(CC)CC)C.[NH:23]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@H:24]([C:34](ON1C(=O)CCC1=O)=[O:35])[CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O>[NH:23]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@H:24]([C:34]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])=[O:35])[CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 170358L-Asparagine, monohydrateHCID 12879025Boc-Ser(Bzl)-OSu

생성물 1

HCID 15283199Boc-Ser(Bzl)-Asn-OH수율 71.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

In 80 ml of H2O was suspended 4.50 g of H-Asn-OH.H2O, followed by addition of 80 ml of a THF solution containing 4.20 ml of triethylamine and 14.13 g of Boc-Ser(Bzl)-OSu under ice-cooling. The mixture was stirred at room temperature for 20 hours, after which the THF was distilled off. The residual aqueous solution was adjusted to pH 3 with 1M citric acid under ice-cooling and the resulting oily product was extracted with 200 ml of ethyl acetate. The extract was washed with 50 ml of saturated aqueous sodium chloride solution twice, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was treated with ether/petroleum ether (2:1) for solidification and the resultant powder was reprecipitated from methanol-isopropyl ether to give 8.74 g of Boc-Ser(Bzl)-Asn-OH (yield 71.2%).

후처리

  1. temperaturecooling
  2. distillationafter which the THF was distilled off
  3. temperaturecooling
  4. extractionthe resulting oily product was extracted with 200 ml of ethyl acetate
  5. washThe extract was washed with 50 ml of saturated aqueous sodium chloride solution twice
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionThe residue was treated with ether/petroleum ether (2:1) for solidification
  9. customthe resultant powder was reprecipitated from methanol-isopropyl ether

출처 및 근거

ORD 기록
ord-5fa9ef88a1ae49ccabd1b265975312d0
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428129

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