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

HRID 1913315

반응식

HRID 1913315 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-231b7b358c8d4d6b82149181a3dfba60
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609681B2

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