4-Iodobenzoyl chloride → 1-Iodo-4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}benzene

HRID 1519656Notes

Reaction equation

HRID 1519656 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.Cl.[CH3:21][NH:22][C:23](=[O:31])[C@H:24]([C:27](=[O:30])[O:28][CH3:29])[NH:25][CH3:26]>C(Cl)(Cl)Cl>[I:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](=[O:16])[N:25]([CH:24]([C:23]([NH:22][CH3:21])=[O:31])[C:27]([O:28][CH3:29])=[O:30])[CH3:26])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 743734-Iodobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 86679246N,N2,O-trimethyl-3-oxoserinamide hydrochloride2×

Product 1

HCID 712681491-Iodo-4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}benzeneYield 73.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

DIPEA (27 mL) was added to a chloroform (0.20 L) suspension of 4-iodobenzoyl chloride (13 g) and N,N2,O-trimethyl-3-oxoserinamide hydrochloride (Intermediate 5-2, 10 g) under ice cooling, and the mixture was stirred for 4 hours at room temperature, whereafter the reaction mixture was concentrated. The resulting residue was purified by OH type silica gel column chromatography (gradient elution with hexane/ethyl acetate=70/30→0/100) to obtain 1-iodo-4-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}benzene (Intermediate 6-2, white solid) (14 g, 68%).

Workup

  1. concentrationwas concentrated
  2. customThe resulting residue was purified by OH type silica gel column chromatography (gradient elution with hexane/ethyl acetate=70/30→0/100)

Sources & evidence

ORD record
ord-8bb7f4537e264f84b19fbde559ef5845
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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