4-Iodobenzoyl chloride → HCID 71268161, compound

HRID 1519660Notes

Reaction equation

HRID 1519660 reaction equation
CCN(C(C)C)C(C)C.[I:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1.[CH2:20]([O:22][C:23](=[O:32])[C@@:24]([CH3:31])([C:27]([NH:29][CH3:30])=[O:28])[NH:25][CH3:26])[CH3:21]>C(Cl)(Cl)Cl>[CH2:20]([O:22][C:23](=[O:32])[C:24]([N:25]([CH3:26])[C:15]([C:14]1[CH:18]=[CH:19][C:11]([I:10])=[CH:12][CH:13]=1)=[O:16])([CH3:31])[C:27]([NH:29][CH3:30])=[O:28])[CH3:21]

Participants

5

Reactant 3

HCID 743734-Iodobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 86679250HCID 86679250, compound2×

Product 1

HCID 71268161HCID 71268161, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

DIPEA (0.34 mL) and 4-iodobenzoyl chloride (0.13 g) were added to a chloroform (2.3 mL) solution of O-ethyl-N,N2,2-trimethyl-3-oxoserinamide (Intermediate 9-1, 0.25 g) under ice cooling, and the mixture was stirred for 40 minutes at room temperature, whereafter the reaction mixture was concentrated. The resulting residue was purified by NH type silica gel column chromatography (gradient elution with hexane/ethyl acetate=70/30→35/65) to obtain 1-{[1-ethoxy-2-methyl-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}-4-iodobenzene (Intermediate 10-1, yellow oil) (0.20 g, 72%).

Workup

  1. concentrationwas concentrated
  2. customThe resulting residue was purified by NH type silica gel column chromatography (gradient elution with hexane/ethyl acetate=70/30→35/65)

Sources & evidence

ORD record
ord-a02e4788e45e48f59b6742976598651a
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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