1-Aminocyclopropane-1-carboxylic acid → HCID 24798412, compound

HRID 1715467Notes

Reaction equation

HRID 1715467 reaction equation
[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[C:23]([O:25][CH:26](Cl)[CH:27](C)C)=[O:24].[C:31]1([CH2:37][C:38]([OH:40])=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)(Cl)Cl>[C:31]1([CH2:37][C:38]([O:40][CH2:27][CH2:26][O:25][C:23]([NH:7][C:3]2([C:4]([OH:6])=[O:5])[CH2:2][CH2:1]2)=[O:24])=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 5

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 999Phenylacetic AcidHCID 6397ChlorotrimethylsilaneHCID 81531Diisopropylethylamine2×HCID 27333261-Chloro-2-Methylpropyl Chloroformate

Product 1

HCID 24798412HCID 24798412, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Following the general procedure for the one pot synthesis, ACPC (1.02 g, 9.8 mmol) was reacted with chlorotrimethylsilane (2.48 mL, 19.7 mmol) in anhydrous chloroform in the presence of DIEA (3.64 mL, 19.7 mmol). Subsequent reaction of the intermediate with 1-chloro-2-methylpropyl chloroformate (1.6 mL, 14.8 mmol) followed by a mixture of DIEA (3.64 mL, 19.7 mmol) and phenylacetic acid (2.6 g, 19.7 mmol) provided 0.560 g (14.4% yield) the title compound (20) as a yellow solid after aqueous work-up and mass-guided preparative HPLC purification. M.p: 142.1-145.6° C. 1H NMR (CDCl3, 400 MHz): δ=7.33 (m, 5H), 6.81 (q, 1H), 5.31 (s, 1H), 3.61 (s, 2H), 1.63 (m, 2H), 1.47 (d, 3H), 1.28 (m, 2H). MS (ESI) m/z 330.08 (M+Na)+.

Sources & evidence

ORD record
ord-061096a2ea7d4aea87b3cb62b9423ff3
Source dataset
uspto-grants-2010_09
Patent number
US07799829B2

Reaction notes

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