Acetonitrile → HCID 178473496, compound

HRID 386948Notes

Reaction equation

HRID 386948 reaction equation
C1C[C@H](C(O)=O)CC[C@H]1CN.[C:12]([O:20][CH:21]([O:23][C:24]([NH:26][CH2:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([C:34]([OH:36])=[O:35])[CH2:30][CH2:29]1)=[O:25])[CH3:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+:41].C(#N)C>O>[C:12]([O:20][CH:21]([O:23][C:24]([NH:26][CH2:27][C@H:28]1[CH2:29][CH2:30][C@H:31]([C:34]([O-:36])=[O:35])[CH2:32][CH2:33]1)=[O:25])[CH3:22])(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1.[Na+:41]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 178473494HCID 178473494, compoundHCID 178511262HCID 178511262, compound

Product 1

HCID 178473496HCID 178473496, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following the general nucleophilic carbamoylation procedure for the formation of the corresponding sodium carboxylates of acyloxyalkyl carbamates of tranexamic acid, 2.096 g (6.0 mmol) of trans-4-{[1-(benzoyloxy)ethoxycarbonyl]aminomethyl}-cyclohexanecarboxylic acid 23 was reacted with 504.1 mg (6.0 mmol) of sodium bicarbonate (NaHCO3) in 20 mL of a mixture of acetonitrile and water (1:1) to yield 2.23 g (quant.) of the title compound 24 as a colorless powder. 1H NMR (400 MHz, DMSO-d6): δ=0.72-0.86 (m, 2H), 1.08-1.21 (m, 2H), 1.22-1.32 (m, 1H), 1.53 (d, J=5.6 Hz, 31-1), 1.59-1.84 (br. m, 5H), 2.73-2.86 (m, 2H), 6.88 (q, J=5.6 Hz, 1H), 7.47-7.56 (m, 3H), 7.64-7.70 (m, 1H), 7.89-7.94 (m, 2H). MS (ESI) m/z 373.10 (M+Na)+; 348.12 (M−H)−.

Sources & evidence

ORD record
ord-0b82d88265fa49e185af88c6057d2662
Source dataset
uspto-grants-2013_02
Patent number
US08372881B2

Reaction notes

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