Chloroacetyl chloride → 3-(N'-(Chloroacetyl)-L-alaninyl)amino-2,3-dihydro-1-methyl-5-phenyl-1H-1,4-benzodiazepin-2-one

HRID 133303Notes

Reaction equation

HRID 133303 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][CH:7]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[CH:20]=[CH:21][CH:22]=[CH:23][C:10]=2[N:9]([CH3:24])[C:8]1=[O:25])=[O:5])[CH3:3].[Cl:26][CH2:27][C:28](Cl)=[O:29]>C(Cl)Cl>[Cl:26][CH2:27][C:28]([NH:1][C@H:2]([C:4]([NH:6][CH:7]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[CH:20]=[CH:21][CH:22]=[CH:23][C:10]=2[N:9]([CH3:24])[C:8]1=[O:25])=[O:5])[CH3:3])=[O:29]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 235527623-(L-alaninyl)amino-2,3-dihydro-1-methyl-5-phenyl-1H-1,4-benzodiazepin-2-one

Product 1

HCID 229845693-(N'-(Chloroacetyl)-L-alaninyl)amino-2,3-dihydro-1-methyl-5-phenyl-1H-1,4-benzodiazepin-2-oneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(L-alaninyl)amino-2,3-dihydro-1-methyl-5-phenyl-1H-1,4-benzodiazepin-2-one (20.0 mg, 0.0595 mmol), α-chloroacetyl chloride (5.9 uL, 0.0744 mmol) and piperidinylmethyl polystyrene (59.5 mg, 3.6 nm ol/g (Fluka)) in 1 mL of methylene chloride were shaken for 20 min. Aminomethyl polystyrene (58 mg, 3.0 mmol/g (Advanced Chemtech)) was then added and the reaction mixture was shaken for an additional 15 min. and filtered. Removal of the solvent under reduced pressure provided 23.9 mg (98%) of the crude product which was used without further purification.

Workup

  1. filtrationfiltered
  2. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-2f0697076195409ab97ff911c292d53f
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Reaction notes

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