Dimethylformamide → 61350-60-5

HRID 2258492Notes

Reaction equation

HRID 2258492 reaction equation
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3](O)=[O:4].CN(C=O)C.C(Cl)(=O)C([Cl:27])=O>C(Cl)Cl>[C:9]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([Cl:27])=[O:4])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 1103285461350-60-5

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of CBZ-L-Pro-OH (0.62 g, 2.49 mmol) and a drop of DMF in methylene chloride (10 ml) under argon was added oxalyl chloride (0.26 ml; 2.99 mmol) which resulted in a vigorous evolution of gas. After the evolution of gas ceased, the reaction was stirred for an additional 30 minutes. The reaction was then concentrated to give, as a light yellow oil, N-carbobenzoxy-L-prolyl chloride (CBZ-L-Pro-Cl).

Workup

  1. customresulted in a vigorous evolution of gas
  2. concentrationThe reaction was then concentrated

Sources & evidence

ORD record
ord-d2d0cf91f59943f0b8086afeff3628b3
Source dataset
uspto-grants-1997_08
Patent number
US05661167

Reaction notes

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