Tetrahydrofuran → Boc-Ser(Bzl)-Asn-OH

HRID 1721009ノート

反応式

HRID 1721009 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 15283199Boc-Ser(Bzl)-Asn-OH収率 71.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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%). mp: 138°-139° C. [α]D22 : 10.2° (c=1, DMF) Rf: 0.54 (chloroform:methanol:acetic acid=7:2:1) Amino acid analysis: Asp 1.14 (1), Ser 0.86 (1)

後処理

  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

出典と根拠

ORDレコード
ord-84a8ceee880146abad6d3ea619894db0
出典データセット
uspto-grants-1996_04
特許番号
US05508382

反応ノート

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