1-Aminocyclopropane-1-carboxylic acid → HCID 24798316, compound

HRID 492046Notes

Reaction equation

HRID 492046 reaction equation
[CH2:1]1[C:3]([NH2:7])([C:4]([OH:6])=[O:5])[CH2:2]1.[C:8]([O:16][CH2:17][CH2:18][O:19][C:20](ON1C(=O)CCC1=O)=[O:21])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:9]1([C:8]([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])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 86618757HCID 86618757, compound

Product 1

HCID 24798316HCID 24798316, compoundYield 38.5%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, ACPC (121 mg, 1.1 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl benzoate (341 mg, 1.0 mmol) were reacted to provide 113 mg (35% yield) of the title compound (4) as a white powder after work-up and mass-guided preparative HPLC purification. M.p.: 173.8-175.8° C. 1H NMR (CD3CN, 400 MHz): δ=8.00 (d, 2H), 7.61 (t, 1H), 7.50 (t, 2H), 6.99 (q, 1H), 6.31 (s, 0.8H), 6.01 (br s, 0.2H), 1.60 (d, 3H), 1.42 (m, 2H), 1.09 (m, 2H). MS (ESI) m/z 294.10 (M+H)+; 311.12 (M+NH4)+; 316.11 (M+Na)+; 292.12 (M−H)−.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-e952050456c0477da0b0e80feb2dc85e
Source dataset
uspto-grants-2009_05
Patent number
US07531572B2

Reaction notes

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