1-Aminocyclopropane-1-carboxylic acid → HCID 68510996, compound

HRID 492056Notes

Reaction equation

HRID 492056 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]([CH3:29])[CH3:28])=[O:24].[C:31]([OH:41])(=[O:40])/[CH:32]=[CH:33]/[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)(Cl)Cl>[C:34]1(/[CH:33]=[CH:32]/[C:31]([O:41][CH:26]([O:25][C:23]([NH:7][C:3]2([C:4]([OH:6])=[O:5])[CH2:2][CH2:1]2)=[O:24])[CH:27]([CH3:29])[CH3:28])=[O:40])[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 5

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 6397ChlorotrimethylsilaneHCID 81531Diisopropylethylamine2×HCID 444539Cinnamic AcidHCID 27333261-Chloro-2-Methylpropyl Chloroformate

Product 1

HCID 68510996HCID 68510996, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Following the general procedure for the one pot synthesis, ACPC (2.5 g, 24.6 mmol) was reacted with chlorotrimethylsilane (6.25 mL, 49.2 mmol) in anhydrous chloroform (25 mL) in the presence of DIEA (9.1 mL, 49.4 mmol). Subsequent reaction of the intermediate with 1-chloro-2-methylpropyl chloroformate (5.0 mL, 37 mmol) followed by a mixture of DIEA (9.1 mL, 49.4 mmol) and trans-cinnamic acid (7.1 g, 48 mmol) provided 0.406 g (12.2% yield) of the title compound (18) as a light-yellow solid after aqueous work-up and mass-guided preparative HPLC purification. M.p: 147.8-150.2° C. 1H NMR (CDCl3, 400 MHz): δ=7.72-7.68 (d, 1H, J=15.6), 7.51 (br s, 2H), 7.37 (m, 3H), 6.71 (d, 1H), 6.42 (d, 1H J=16), 5.51 (s, 0.3H), 5.31 (s, 0.7H), 2.11 (m, 1H), 1.58 (m, 2H), 1.24 (m, 2H), 1.02 (d, 6H). MS (ESI) m/z 345.98 (M−H)−.

Sources & evidence

ORD record
ord-26354139d0884b8c9e5f7ea3998aac08
Source dataset
uspto-grants-2009_05
Patent number
US07531572B2

Reaction notes

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