1-Aminocyclopropane-1-carboxylic acid → HCID 24798409, compound

HRID 492051Notes

Reaction equation

HRID 492051 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])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>>[C:8]([O:16][CH2:17][CH2:18][O:19][C:20]([NH:7][C:3]1([C:4]([OH:6])=[O:5])[CH2:2][CH2:1]1)=[O:21])(=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 86618760HCID 86618760, compound

Product 1

HCID 24798409HCID 24798409, compoundYield 15.4%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, ACPC (0.530 g, 5.2 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl heptanoate (1 g, 4.03 mmol) were reacted to provide 0.148 g (15.4% yield) of the title compound (13) as a white powder after work-up and mass-guided preparative HPLC purification. M.p.: 112.6-113.2° C. 1H NMR (CDCl3, 400 MHz): δ=6.79 (q, 1H), 5.81 (s, 0.2H), 5.4 (s, 0.8H), 2.3 (m, 2H), 1.64 (m, 4H), 1.51 (d, 3H), 1.32 (m, 8H), 0.98 (t, 3H). MS (ESI) m/z 324.05 (M+Na)+; 300.04 (M−H)−.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-2ce90bc75c5c485da1b57931e193ac3a
Source dataset
uspto-grants-2009_05
Patent number
US07531572B2

Reaction notes

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