1-Aminocyclopropane-1-carboxylic acid → HCID 24798414, compound

HRID 1715469Notes

Reaction equation

HRID 1715469 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]12([C:41]([OH:43])=[O:42])[CH2:40][CH:35]3[CH2:36][CH:37]([CH2:39][CH:33]([CH2:34]3)[CH2:32]1)[CH2:38]2>C(Cl)(Cl)Cl>[C:31]12([C:41]([O:43][CH2:27][CH2:26][O:25][C:23]([NH:7][C:3]3([C:4]([OH:6])=[O:5])[CH2:2][CH2:1]3)=[O:24])=[O:42])[CH2:40][CH:35]3[CH2:36][CH:37]([CH2:39][CH:33]([CH2:34]3)[CH2:32]1)[CH2:38]2

Participants

7

Reactant 5

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 6397ChlorotrimethylsilaneHCID 132351-Adamantanecarboxylic acidHCID 81531Diisopropylethylamine2×HCID 27333261-Chloro-2-Methylpropyl Chloroformate

Product 1

HCID 24798414HCID 24798414, compoundYield 6.4%

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 admantane carboxylic acid (3.5 g, 19.7 mmol) provided 0.220 g (6.4% yield) of the title compound (22) as a white solid after aqueous work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.81 (q, 1H), 5.62 (s, 0.2H), 5.38 (s, 0.8H), 2.09 (m, 4H), 1.93 (m, 6H), 1.72 (m, 6H), 1.61 (s, 2H), 1.52 (d, 3H), 1.37 (br s, 2H). MS (ESI) m/z 374.01 (M+H)+, M−H=350.04 (M−H)−.

Sources & evidence

ORD record
ord-4db6f7004fc24f6287c3a27e2d89b1f7
Source dataset
uspto-grants-2010_09
Patent number
US07799829B2

Reaction notes

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