2-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-(2-isopropoxybenzyl)-n-methoxy-acetamide → 2-Hydroxy-3-[(2-isopropoxy-benzyl)-methoxy-carbamoyl]-acrylic acid methyl ester

HRID 2214622Notes

Reaction equation

HRID 2214622 reaction equation
C[C:2]1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]([CH3:23])[CH3:22])[O:11][CH3:12])=[O:9])[C:4](=[O:24])[O:3]1>CO>[CH3:2][O:3][C:4](=[O:24])[C:5]([OH:6])=[CH:7][C:8](=[O:9])[N:10]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH:21]([CH3:22])[CH3:23])[O:11][CH3:12]

Participants

3

Reactant 1

HCID 738555562-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-n-(2-isopropoxybenzyl)-n-methoxy-acetamide

Product 1

HCID 723950702-Hydroxy-3-[(2-isopropoxy-benzyl)-methoxy-carbamoyl]-acrylic acid methyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2,2-Dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-(2-isopropoxybenzyl)-N-methoxy-acetamide, prepared using the methods described in the previous examples, was treated with methanol as described in the preparation of Compound 44-D and gave the title ester as a white syrup (62% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.33 (6H, d, J=6 Hz, CH3), 3.68 (3H, s, OCH3), 3.89 (3H, s, OCH3), 4.59 (1H, m, CH), 4.9 (2H, s, NCH2), 6.50 (1H, s, CH), 6.88 (2H, m, aromatics), 7.24 (2H, m, aromatics). HRMS (MAB N2) calculated for C16H21NO6, [M]+: 323.136888. found: 323.136700.

Workup

  1. customas described in the preparation of Compound 44-D

Sources & evidence

ORD record
ord-38c3d2f1069540169ceb91323ee63520
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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