1-Aminocyclopropane-1-carboxylic acid → 1-{[(3,4-Dimethoxyphenylcarbonyloxy)ethoxy]carbonylamino}cyclopropanecarboxylic Acid

HRID 492052Notes

Reaction equation

HRID 492052 reaction equation
[CH2:1]1[C:3]([NH2:7])([C:4]([OH:6])=[O:5])[CH2:2]1.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[C:13]([O:15][CH2:16][CH2:17][O:18][C:19](ON1C(=O)CCC1=O)=[O:20])=[O:14]>>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:13]([O:15][CH2:16][CH2:17][O:18][C:19]([NH:7][C:3]2([C:4]([OH:6])=[O:5])[CH2:2][CH2:1]2)=[O:20])=[O:14])[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]

Participants

3

Reactant 2

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 86618761(2,5-Dioxoazolidinyloxycarbonyloxy)ethyl 3,4-dimethoxybenzoate

Product 1

HCID 685139401-{[(3,4-Dimethoxyphenylcarbonyloxy)ethoxy]carbonylamino}cyclopropanecarboxylic AcidYield 72.9%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, ACPC (0.122 g, 1.21 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl 3,4-dimethoxybenzoate (0.4 g, 1.01 mmol) were reacted to provide 0.260 g (68% yield) of the title compound (14) as a white powder after work-up and mass-guided preparative HPLC purification. M.p.: 171.8-173.6° C. 1H NMR (CDCl3, 400 MHz): δ=7.69 (d, 1H), 7.47 (s, 1H), 7.13 (d, 1H), 6.83 (d, 1H), 5.52 (s, 0.3H), 5.43 (s, 0.7H), 3.98 (d, 6H), 1.62 (m, 5H), 1.31 (br s, 2H). MS (ESI) m/z 375.99 (M+Na)+; 352.02 (M−H)−.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-177d2a3a65fd4ab9b3c00983dc5dd962
Source dataset
uspto-grants-2009_05
Patent number
US07531572B2

Reaction notes

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