1-Aminocyclopropane-1-carboxylic acid → HCID 24798411, Verbindung

HRID 492054

Reaktionsgleichung

Reaktionsgleichung von HRID 492054
[CH2:1]1[C:3]([NH2:7])([C:4]([OH:6])=[O:5])[CH2:2]1.Cl[Si](C)(C)C.CCN(C(C)C)C(C)C.Cl[CH:23]([O:25][C:26](Cl)=[O:27])[CH3:24].[C:29]([OH:39])(=[O:38])/[CH:30]=[CH:31]/[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)(Cl)Cl>[C:32]1(/[CH:31]=[CH:30]/[C:29]([O:39][CH2:24][CH2:23][O:25][C:26]([NH:7][C:3]2([C:4]([OH:6])=[O:5])[CH2:2][CH2:1]2)=[O:27])=[O:38])[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Komponenten

7

Edukt 5

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 6397ChlorotrimethylsilaneHCID 81531Diisopropylethylamine2×HCID 444539Cinnamic AcidHCID 5213051-Chloroethyl chloroformate

Produkt 1

HCID 24798411HCID 24798411, VerbindungAusbeute 16,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Following the general procedure for the one pot synthesis, ACPC (0.4 g, 3.9 mmol) was reacted with chlorotrimethylsilane (0.99 mL, 7.88 mmol) in anhydrous chloroform (10 mL) in the presence of DIEA (1.45 mL, 7.8 mmol). Subsequent reaction of the intermediate with 1-chloroethylchloroformate (0.83 mL, 5.85 mmol) followed by a mixture of DIEA (1.45 mL, 7.8 mmol) and trans-cinnamic acid (1.16 g, 7.88 mmol) provided 0.200 g (16.6% yield) of the title compound (16) as a buff-colored solid after aqueous work-up and mass-guided preparative HPLC purification. M.p: 169.3-172.2° C. 1H NMR (CDCl3, 400 MHz): δ=7.71-7.67 (d, 1H, J=15.6), 7.50 (d, 2H), 7.38 (m, 3H), 6.95 (q, 1H), 6.40 (d, 1H, J=16), 5.58 (s, 0.3H), 5.34 (s, 0.7H), 1.60-1.54 (m, 5H), 1.27-1.24 (m, 2H). MS (ESI) m/z 342.00 (M+Na)+; 318.02 (M−H)−.

Quellen und Nachweise

ORD-Eintrag
ord-c299cb0edf144df894a1df6805575872
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531572B2

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