1-Aminocyclopropane-1-carboxylic acid → HCID 24798315, compound

HRID 1715456Notes

Reaction equation

HRID 1715456 reaction equation
[CH2:1]1[C:3]([NH2:7])([C:4]([OH:6])=[O:5])[CH2:2]1.[CH3:8][C:9]1[CH:30]=[CH:29][CH:28]=[CH:27][C:10]=1[C:11]([O:13][CH2:14][CH2:15][O:16][C:17](ON1C(=O)CCC1=O)=[O:18])=[O:12]>>[CH3:8][C:9]1[CH:30]=[CH:29][CH:28]=[CH:27][C:10]=1[C:11]([O:13][CH2:14][CH2:15][O:16][C:17]([NH:7][C:3]1([C:4]([OH:6])=[O:5])[CH2:2][CH2:1]1)=[O:18])=[O:12]

Participants

3

Reactant 2

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 86618756HCID 86618756, compound

Product 1

HCID 24798315HCID 24798315, compoundYield 43.3%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, ACPC (121 mg, 1.2 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl 2-methylbenzoate (321 mg, 1.0 mmol) were reacted to provide 133 mg (43% yield) of the title compound (3) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=7.85 (d, 1H), 7.40 (t, 1H), 7.21 (t, 2H), 7.01 (q, 1H), 5.79 (br s, 0.3H), 5.41 (s, 0.7H), 2.58 (s, 3H), 1.60 (m, 5H), 1.30 (m, 2H). MS (ESI) m/z 325.17 (M+NH4)+; 330.12 (M+Na)+; 306.15 (M−H)−.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-13eec135907d42439e30e0ecde309399
Source dataset
uspto-grants-2010_09
Patent number
US07799829B2

Reaction notes

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