1-Aminocyclopropane-1-carboxylic acid → HCID 24798321, compound

HRID 1715458Notes

Reaction equation

HRID 1715458 reaction equation
[CH2:1]1[C:3]([NH2:7])([C:4]([OH:6])=[O:5])[CH2:2]1.[CH3:8][CH:9]([CH3:25])[C:10]([O:12][CH2:13][O:14][C:15](ON1C(=O)CCC1=O)=[O:16])=[O:11]>>[C:10]([O:12][CH2:13][O:14][C:15]([NH:7][C:3]1([C:4]([OH:6])=[O:5])[CH2:2][CH2:1]1)=[O:16])(=[O:11])[CH:9]([CH3:25])[CH3:8]

Participants

3

Reactant 2

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 86618758HCID 86618758, compound

Product 1

HCID 24798321HCID 24798321, compoundYield 44%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, ACPC (121 mg, 1.2 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)methyl 2-methylpropanoate (259 mg, 1.0 mmol) were reacted to provide 107 mg (44% yield) of the title compound (9) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=5.99 (br s, 0.2H), 5.78 (br s, 0.4H), 5.73 (s, 1.6H), 5.59 (s, 0.8H), 2.59 (m, 1H), 1.62 (m, 2H), 1.31 (m, 2H), 1.19 (d, 6H). MS (ESI) m/z 246.10 (M+H)+; 263.11 (M+NH4)+; 268.09 (M+Na)+; 244.11 (M−H)−.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-87cefd6c5ec24823b4fc2d32fae1bd24
Source dataset
uspto-grants-2010_09
Patent number
US07799829B2

Reaction notes

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