1-Aminocyclopropane-1-carboxylic acid → 1-[(Cyclohexylcarbonyloxyethoxy)carbonylamino]cyclopropanecarboxylic Acid

HRID 492048Notes

Reaction equation

HRID 492048 reaction equation
[CH2:1]1[C:3]([NH2:7])([C:4]([OH:6])=[O:5])[CH2:2]1.[CH:8]1([C:14]([O:16][CH2:17][CH2:18][O:19][C:20](ON2C(=O)CCC2=O)=[O:21])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH:8]1([C:14]([O:16][CH2:17][CH2:18][O:19][C:20]([NH:7][C:3]2([C:4]([OH:6])=[O:5])[CH2:2][CH2:1]2)=[O:21])=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 86618759(2,5-Dioxoazolidinyloxycarbonyloxy)ethyl cyclohexanecarboxylate

Product 1

HCID 247983221-[(Cyclohexylcarbonyloxyethoxy)carbonylamino]cyclopropanecarboxylic AcidYield 16.4%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, ACPC (426 mg, 4.2 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl cyclohexanecarboxylate (1.1 g, 3.5 mmol) were reacted to provide 172 mg (16% yield) of the title compound (10) as a white powder after work-up and mass-guided preparative HPLC purification. M.p.: 123.6-125.3° C. 1H NMR (CDCl3, 400 MHz): δ=9.92 (br s, 1H), 6.76 (q, 1H), 6.34 (br s, 0.3H), 5.59 (s, 0.7H), 2.27 (m, 1H), 1.10-1.95 (m, 17H). MS (ESI) nm/z 317.15 (M+NH4)+; 322.13 (M+Na)+; 298.15 (M−H)−.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-fb5425e713bc4a24b81d5203b6e37b20
Source dataset
uspto-grants-2009_05
Patent number
US07531572B2

Reaction notes

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