Pivaloyl chloride → Methyl 2-chloro-5-(pivalamidomethyl)benzoate

HRID 1469720Notes

Reaction equation

HRID 1469720 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10].CCN(C(C)C)C(C)C.[C:24](Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>C1COCC1>[Cl:14][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][NH:2][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 66524840Methyl 5-(aminomethyl)-2-chlorobenzoate--hydrogen chloride (1/1)

Product 1

HCID 67971274Methyl 2-chloro-5-(pivalamidomethyl)benzoateYield 117.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure described in step-2 of Intermediate-2 using methyl 5-(aminomethyl)-2-chlorobenzoate hydrochloride (1.80 g, 6.00 mmol), DIPEA (3.096 g, 2.4 mmol) and pivaloyl chloride (1.2 mL, 9.0 mmol) in THF (20 mL) to afford 2.0 g of the title product. 1H NMR (300 MHz, DMSO d6): 8.16 (m, 1H), 7.65 (s, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.41 (d, J=8.4 Hz, 1H), 4.25 (d, J=5.7 Hz, 2H), 3.85 (s, 3H), 1.15 (s, 9H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-c7f92b8771ea4b50b7d66da2f6c25668
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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