Acetonitrile → HCID 178454730, compound

HRID 898374Notes

Reaction equation

HRID 898374 reaction equation
C1C[C@H](C(O)=O)CC[C@H]1CN.[CH3:12][CH:13]([CH3:33])[C:14]([O:16][C@@H:17]([O:19][C:20]([NH:22][CH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([C:30]([OH:32])=[O:31])[CH2:26][CH2:25]1)=[O:21])[CH3:18])=[O:15].C(=O)(O)[O-].[Na+:38].C(#N)C>O>[CH3:12][CH:13]([CH3:33])[C:14]([O:16][C@@H:17]([O:19][C:20]([NH:22][CH2:23][C@H:24]1[CH2:25][CH2:26][C@H:27]([C:30]([O-:32])=[O:31])[CH2:28][CH2:29]1)=[O:21])[CH3:18])=[O:15].[Na+:38]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 178454728HCID 178454728, compoundHCID 178511262HCID 178511262, compound

Product 1

HCID 178454730HCID 178454730, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following the general procedure for the formation of the corresponding sodium carboxylates of acyloxyalkyl carbamates of tranexamic acid, 90.0 mg (0.2854 mmol) of (+)-trans-4-({[(1S)-1-(2-methylpropanoyloxy)ethoxy]carbonylamino}methyl)-cyclohexanecarboxylic acid 15 was reacted with 24.0 mg (0.2854 mmol) of sodium bicarbonate (NaHCO3) in 4 mL of a mixture of acetonitrile and water (1:1) to yield 96.3 mg (quant.) of the title compound 16 as a colorless powder. The enantiomeric excesses were determined with an analytical Waters 2690/ZQ LC/MS apparatus using a ChiralPak AD-RH column, an isocratic eluent consisting of 30% acetonitrile/70% water/0.05% formic acid, and a flowrate of 60 μL/min (Rf=12.1 min; e.e.=98.5%). 1H NMR (400 MHz, DMSO-d6): δ=0.72-0.84 (br. m, 2H), 1.057 (d, J=6.4 Hz, 3H), 1.059 (d, J=6.8 Hz, 3H), 1.20-1.32 (br. m, 3H), 1.38 (d, J=5.2 Hz, 3H), 1.59-1.73 (br. m, 3H), 1.75-1.83 (m, 2H), 2.43-2.53 (m, 1H), 2.72-2.84 (br. m, 2H), 6.62 (q, J=5.6 Hz, 1H), 7.42 (t, J=5.6 Hz, 1H). MS (EST) m/z 338.16 (M+Na)+; 314.12 (M−H)−.

Sources & evidence

ORD record
ord-c8f2b42893024e9fbdf8b42e752b16fa
Source dataset
uspto-grants-2008_04
Patent number
US07351740B2

Reaction notes

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