Dimethylformamide → Methyl (S)-2-benzyloxycarbonylamino-3-chlorocarbonylpropionate

HRID 1913315

反応式

HRID 1913315 の反応式
[CH3:1][O:2][C:3]([C@@H:5]([NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:6][C:7](O)=[O:8])=[O:4].CN(C=O)C.C(Cl)(=O)C([Cl:29])=O>C1COCC1>[CH2:14]([O:13][C:11]([NH:10][C@@H:5]([CH2:6][C:7]([Cl:29])=[O:8])[C:3]([O:2][CH3:1])=[O:4])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 7021783Z-Asp-OMe

生成物 1

HCID 11055664Methyl (S)-2-benzyloxycarbonylamino-3-chlorocarbonylpropionate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Z-asp-OMe (175 g, 622 mmol) was dissolved in THF (1750 ml) and admixed with 2 ml of DMF. 86.9 g (684 mmol) of oxalyl chloride were dissolved in 200 ml of THF (slightly exothermic), cooled back to room temperature (RT) and added dropwise to the solution of the amino acid over 1 hour (h). After a further hour at RT, the solution was initially sparged with nitrogen for 10 min, concentrated on a rotary evaporator at a maximum of 30° C. and coevaporated repeatedly with toluene. The resulting dirty white solid was dried to constant weight under in-house vacuum (about 1.5 mbar) and reacted further without further purification. Yield: 186.6 g (quantitative).

後処理

  1. waitAfter a further hour at RT
  2. customthe solution was initially sparged with nitrogen for 10 min
  3. concentrationconcentrated on a rotary evaporator at a maximum of 30° C.
  4. customThe resulting dirty white solid was dried to constant weight under in-house vacuum (about 1.5 mbar)
  5. customreacted further without further purification

出典と根拠

ORDレコード
ord-231b7b358c8d4d6b82149181a3dfba60
出典データセット
uspto-grants-2013_12
特許番号
US08609681B2

関連ノート

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