1-Aminocyclopropane-1-carboxylic acid → 1-(1-Isobutyryloxy-2-methyl-propoxycarbonylamino)-cyclopropanecarboxylic Acid
Reaction equation
[CH2:1]1[C:3]([NH2:7])([C:4]([OH:6])=[O:5])[CH2:2]1.[CH3:8][CH:9]([CH3:28])[C:10]([O:12][CH:13]([O:17][C:18](ON1C(=O)CCC1=O)=[O:19])[CH:14]([CH3:16])[CH3:15])=[O:11]>>[C:10]([O:12][CH:13]([O:17][C:18]([NH:7][C:3]1([C:4]([OH:6])=[O:5])[CH2:2][CH2:1]1)=[O:19])[CH:14]([CH3:15])[CH3:16])(=[O:11])[CH:9]([CH3:28])[CH3:8]Participants
3
Procedure
Following the general procedure for the synthesis of acyloxyalkyl carbamates, ACPC (121 mg, 1.2 mmol) and 1-(2,5-dioxoazolidinyloxycarbonyloxy)-2-methylpropyl 2-methylpropanoate (301 mg, 1.0 mmol) were reacted to provide 148 mg (51% yield) of the title compound (2) as a white powder after work-up and mass-guided preparative HPLC purification. M.p.: 127.4-129.0° C. 1H NMR (CDCl3, 400 MHz): δ=6.59 (d, 1H), 5.68 (br s, 0.3H), 5.39 (s, 0.7H), 2.58 (m, 1H), 2.01 (m, 1H), 1.61 (m, 2H), 1.30 (m, 2H), 1.19 (d, 3H), 1.18 (d, 3H), 0.99 (d, 6H). MS (ESI) m/z 305.20 (M+NH4)+; 310.15 (M+Na)+; 286.21 (M−H)−.
Workup
- customwere reacted
Sources & evidence
- ORD record
- ord-a390a37c6a9144dab4ba74d2614b2648
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07531572B2
Reaction notes
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