Acetonitrile → HCID 178454745, compound

HRID 734945Notes

Reaction equation

HRID 734945 reaction equation
C1C[C@H](C(O)=O)CC[C@H]1CN.[CH3:12][CH:13]([CH3:35])[C:14]([O:16][CH:17]([O:21][C:22]([NH:24][CH2:25][C@H:26]1[CH2:31][CH2:30][C@H:29]([C:32]([OH:34])=[O:33])[CH2:28][CH2:27]1)=[O:23])[CH:18]([CH3:20])[CH3:19])=[O:15].C(=O)(O)[O-].[Na+:40].C(#N)C>O>[CH3:12][CH:13]([CH3:35])[C:14]([O:16][CH:17]([O:21][C:22]([NH:24][CH2:25][C@H:26]1[CH2:31][CH2:30][C@H:29]([C:32]([O-:34])=[O:33])[CH2:28][CH2:27]1)=[O:23])[CH:18]([CH3:19])[CH3:20])=[O:15].[Na+:40]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 178454743HCID 178454743, compoundHCID 178511262HCID 178511262, compound

Product 1

HCID 178454745HCID 178454745, 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, 3.434 g (10.0 mmol) of trans-4-{[1-(2-methylpropanoyloxy)-2-methylpropoxycarbonyl]aminomethyl}-cyclohexanecarboxylic acid 44 was reacted with 840.1 mg (10.0 mmol) of sodium bicarbonate (NaHCO3) in 60 mL of a mixture of acetonitrile and water (1:2) to yield 3.654 g (quant.) of the title compound 45 as a colorless powder. 1H NMR (400 MHz, DMSO-d6): δ=0.72-0.84 (m, 2H), 0.87-0.92 (m, 6H), 1.04-1.20 (m, 8H), 1.20-1.32 (m, 1H), 1.59-1.73 (m, 3H), 1.74-1.83 (m, 2H), 1.88-1.98 (m, 1H), 2.46-2.56 (m, 1H), 2.72-2.84 (br. m, 2H), 6.42 (d, J=5.6 Hz, 1H), 7.37 (t, J=5.6 Hz, 1H). MS (ESI) m/z 366.14 (M+Na)+; 342.16 (M−H)−.

Sources & evidence

ORD record
ord-040ec7979b384985824b682347ce9ea2
Source dataset
uspto-grants-2009_09
Patent number
US07592369B2

Reaction notes

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