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

HRID 1664705

Reaction equation

HRID 1664705 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-360bc2998965435eb2730a0ec78bba49
Source dataset
uspto-grants-2011_10
Patent number
US08039480B2

Linked notes

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