4-Chlorobenzoyl chloride → HCID 90454299, compound

HRID 57405Notes

Reaction equation

HRID 57405 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]([O:15][C:16](=[O:24])[NH:17][C@@H:18]([CH3:23])[C:19]([NH:21][NH2:22])=[O:20])([CH3:14])([CH3:13])[CH3:12]>C(Cl)Cl>[C:11]([O:15][C:16](=[O:24])[NH:17][C@@H:18]([CH3:23])[C:19]([NH:21][NH:22][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:20])([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 10241974tert-butyl N-((1S)-1-(hydrazinecarbonyl)ethyl)carbamate

Product 1

HCID 90454299HCID 90454299, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Chlorobenzoyl chloride (0.63 mL, 4.92 mmol, 1.0 equiv) was added to a solution of (S)-tert-butyl(1-hydrazinyl-1-oxopropan-2-yl)carbamate (1.0 g, 4.92 mmol) in DCM (25 mL) at 0° C. A white precipitate formed. The mixture was stirred at 0° C. for 1 hour and the reaction mixture was then concentrated in vacuo to give crude (S)-tert-butyl(1-(2-(4-chlorobenzoyl)hydrazinyl)-1-oxopropan-2-yl)carbamate (1.55 g), which was used without purification. 1H NMR (400 MHz, CD3OD) δ 7.85 (d, J=8.7 Hz, 2H), 7.49 (d, J=8.7 Hz, 2H), 4.21 (q, J=7.0 Hz, 1H), 1.45 (s, 9H), 1.41 (d, J=7.2 Hz, 3H). MS m/z 342.1 (M+H)+; Rt-0.69 min.

Workup

  1. customA white precipitate formed
  2. concentrationthe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-8f86b7e42ff34544ae56671e63771a17
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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