Hydrochloric Acid → HCID 67253331, compound

HRID 1944563Notes

Reaction equation

HRID 1944563 reaction equation
C1(C(=[N:14][C:15]([CH3:27])([CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])C2C=CC=CC=2)C=CC=CC=1.Cl>CO.C1COCC1>[NH2:14][C:15]([CH3:27])([CH2:20][C:21]1[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86616983HCID 86616983, compound

Product 1

HCID 67253331HCID 67253331, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a suspension of methyl 2-[(diphenylmethylene)amino]-2-methyl-3-pyridin-4-ylpropanoate from Step B (5.28 g, 14.73 mmol) in 75 ml of 1:1 MeOH/THF was added 6N HCl (3.68 ml, 22.10 mmol). The reaction was concentrated in vacuo after stirring for 1.5 h at rt. Purification using ion exchange chromatography (SCX cartridge) afforded methyl 2-amino-2-methyl-3-pyridin-4-ylpropanoate as a yellow oil (2.76 g, 97%). LCMS [M+H]=195.3. 1H NMR (d4-MeOH) δ 8.43 (dd, J=4.6, 1.6 Hz, 2H), 7.24 (dd, J=4.6, 1.5 Hz, 2H), 3.70 (s, 3H), 3.09 (A of AB, d, J=12.9 Hz, 1H), 2.90 (1 of AB, d, J=13.0 Hz, 1H), 1.39 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customPurification

Sources & evidence

ORD record
ord-2f7c8e02e2fb4168b963c71b8ed85efa
Source dataset
uspto-grants-2013_03
Patent number
US08394837B2

Reaction notes

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