1-Aminocyclopropane-1-carboxylic acid → HCID 24798410, compound

HRID 492053Notes

Reaction equation

HRID 492053 reaction equation
[CH2:1]1[C:3]([NH2:7])([C:4]([OH:6])=[O:5])[CH2:2]1.[C:8]1([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH2:21][O:22][C:23](ON2C(=O)CCC2=O)=[O:24])=[O:18])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:8]1([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH2:21][O:22][C:23]([NH:7][C:3]2([C:4]([OH:6])=[O:5])[CH2:2][CH2:1]2)=[O:24])=[O:18])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 86618762HCID 86618762, compound

Product 1

HCID 24798410HCID 24798410, compoundYield 46%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, ACPC (0.218 g, 2.08 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl 4-phenylbutyrate (0.607 g, 1.73 mmol) were reacted to provide 0.264 g (46% yield) of the title compound (15) as a white semi-solid after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=7.32 (t, 2H), 7.19 (m, 3H), 6.81 (q, 1H), 6.22 (s, 0.3H), 5.43 (s, 0.7H), 2.62 (t, 2H), 2.31 (m, 2H), 1.98 (q, 2H), 1.61 (m, 2H), 1.42 (dd, 3H), 1.23 (m, 2H). MS (ESI) m/z 358.05 (M+Na)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-a67abaa444954dfd8a1ec4450e6bf0d9
Source dataset
uspto-grants-2009_05
Patent number
US07531572B2

Reaction notes

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