Acetonitrile → HCID 178447567, compound

HRID 898377Notes

Reaction equation

HRID 898377 reaction equation
C1C[C@H](C(O)=O)CC[C@H]1CN.[CH3:12][CH:13]([CH3:34])[CH2:14][C:15]([O:17][CH:18]([O:20][C:21]([NH:23][CH2:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([C:31]([OH:33])=[O:32])[CH2:27][CH2:26]1)=[O:22])[CH3:19])=[O:16].C(=O)(O)[O-].[Na+:39].C(#N)C>O>[CH3:12][CH:13]([CH3:34])[CH2:14][C:15]([O:17][CH:18]([O:20][C:21]([NH:23][CH2:24][C@H:25]1[CH2:26][CH2:27][C@H:28]([C:31]([O-:33])=[O:32])[CH2:29][CH2:30]1)=[O:22])[CH3:19])=[O:16].[Na+:39]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 178447565HCID 178447565, compoundHCID 178511262HCID 178511262, compound

Product 1

HCID 178447567HCID 178447567, 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, 1.976 g (6.0 mmol) of trans-4-{[1-(3-methylbutanoyloxy)ethoxycarbonyl]aminomethyl}-cyclohexanecarboxylic acid 19 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 2.11 g (quant.) of the title compound 20 as a colorless powder. 1H NMR (400 MHz, DMSO-d6): δ=0.72-0.84 (m, 2H), 0.89 (d, J=6.4 Hz, 6H), 1.07-1.21 (m, 2H), 1.22-1.32 (m, 1H), 1.38 (d, J=5.2 Hz, 3H), 1.58-1.74 (br. m, 3H), 1.76-1.84 (br. m, 2H), 1.88-2.01 (m, 1H), 2.08-2.20 (m, 2H), 2.74-2.85 (m, 2H), 6.66 (q, J=5.6 Hz, 1H), 7.42 (t, J=6.4 Hz, 1H). MS (ESI) m/z 352.18 (M+Na)+; 328.14 (M−H)−.

Sources & evidence

ORD record
ord-d47bb189eb2b4dc78de255fef09130e7
Source dataset
uspto-grants-2008_04
Patent number
US07351740B2

Reaction notes

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