1-Aminocyclopropane-1-carboxylic acid → HCID 24798413, compound

HRID 492059Notes

Reaction equation

HRID 492059 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].[CH3:31][C:32]1[CH:33]=[CH:34][C:35]([C:38]([OH:40])=[O:39])=[CH:36][CH:37]=1>C(Cl)(Cl)Cl>[CH3:31][C:32]1[CH:37]=[CH:36][C:35]([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:34][CH:33]=1

Participants

7

Reactant 5

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 6397ChlorotrimethylsilaneHCID 7470P-Toluic AcidHCID 81531Diisopropylethylamine2×HCID 27333261-Chloro-2-Methylpropyl Chloroformate

Product 1

HCID 24798413HCID 24798413, compoundYield 14.5%

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 p-toluic acid (2.6 g, 19.7 mmol) provided 0.436 g (14.3% yield) the title compound (21) as a white solid after aqueous work-up and mass-guided preparative HPLC purification. M.p: 177.7-182.5° C. 1H NMR (CDCl3, 400 MHz): δ=7.91 (d, 2H), 7.22 (m, 4H), 7.02 (q, 1H), 5.38 (s, 1H), 2.43 (s, 3H), 1.63 (m, 5H) 1.36 (m, 2H). MS (ESI) m/z 329.93 (M+H)+; 305.97 (M−H)−.

Sources & evidence

ORD record
ord-74f253e3c5d345b0b794ad511063314c
Source dataset
uspto-grants-2009_05
Patent number
US07531572B2

Reaction notes

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