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Tetrahydrofuran → Ethyl (tert-butoxycarbonyl)-D-methionylglycinate

HRID 1277393
ノート
印刷プレビュー

反応式

HRID 1277393 の反応式
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:2]([C:7]([OH:9])=O)[CH2:3][CH2:4][S:5][CH3:6].C1C2[CH:22]3[C:27](=[O:28])N(O)C(=O)C3C1C=C2.C1CC[CH:33]([N:36]=C=NC2CCCCC2)[CH2:32]C1.C1C[O:48]CC1>>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:2]([C:7]([NH:36][CH2:33][C:32]([O:28][CH2:27][CH3:22])=[O:48])=[O:9])[CH2:3][CH2:4][S:5][CH3:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 111051N-(tert-Butyloxycarbonyl)-D-methionine

生成物 1

HCID 12919642Ethyl (tert-butoxycarbonyl)-D-methionylglycinate

反応条件

温度
0 °C

実験手順

In 100 ml of THF are dissolved 10.0 g of BOC-(D)-Met-OH and 7.9 g of HONB, followed by cooling at 0° C. and adding 9.0 g of DCC, and the mixture is stirred at 0° C. for 6 hours. Insoluble matters are filtered out, and 5.9 g of H-Gly-OEt·HCl salt and 5.6 ml of TEA are added to the filtrate, which is then stirred overnight at room temperature. The THF is distilled off and the residue is extracted with 100 ml of AcOEt, followed by washing with water and drying over anhydrous sodium sulphate. The AcOEt is distilled off and the residue is crystallized with petroleum ether. Recrystallization from AcOEt-petroleum ether yields 9.8 g of the desired product, m.p. 55°-56° C., Rf1 =0.70, [α]D21 +2.5° (c=0.67, DMF)

後処理

  1. filtrationInsoluble matters are filtered out
  2. addition5.9 g of H-Gly-OEt·HCl salt and 5.6 ml of TEA are added to the filtrate, which
  3. stirringis then stirred overnight at room temperature
  4. distillationThe THF is distilled off
  5. extractionthe residue is extracted with 100 ml of AcOEt
  6. washby washing with water
  7. dry with materialdrying over anhydrous sodium sulphate
  8. distillationThe AcOEt is distilled off
  9. customthe residue is crystallized with petroleum ether
  10. customRecrystallization from AcOEt-petroleum ether

出典と根拠

ORDレコード
ord-71976bd1ebbc4054ac36f74a196b4d1f
出典データセット
uspto-grants-1981_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04277394

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート