Sodium Hydroxide → HCID 10135545, compound

HRID 51395Notes

Reaction equation

HRID 51395 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([O:23][CH2:24][C:25]([O:27]C)=[O:26])[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][C:15]=2[C:29](=[O:31])[NH2:30])#[N:2].[OH-].[Na+]>C(O)C>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([O:23][CH2:24][C:25]([OH:27])=[O:26])[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][C:15]=2[C:29](=[O:31])[NH2:30])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86756268HCID 86756268, compound

Product 1

HCID 10135545HCID 10135545, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of the {9-[(2-cyanophenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester (110 mg, 0.266 mM) and 0.29 mL (0.29 mM) of 1 N NaOH in 5 mL of ethanol was sonicated for 2 hours at 25° C. The resultant white precipitate was collected by filtration, washed with small amounts of EtOH, diethyl ether, and hexanes, then dried in vacuo to afford 107 mg (95%) of the {9-[(2-cyanophenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, sodium salt as a white powder. 1H NMR (DMSO-d6) δ7.9 (d, 1H, J=8 Hz), 7.6 (br s, 1H), 7.5 (d, 1H, J=8 Hz), 7.45-7.4 (m, 3H), 7.35 (t, 1H, J=8 Hz), 7.25 (t, 1H, J=8 Hz), 7.1 (d, 1H, J=8 Hz), 7.05 (d, 1H, J=8 Hz), 6.55 (d, 1H, J=8 Hz), 6.4 (d, 1H, J=8 Hz), 5.8 (s, 2H), and 4.3 (s, 2H). IR (KBr, cm−1) 2220, 1652, and 1613. MS (ES) m/e 398, 400.

Workup

  1. customwas sonicated for 2 hours at 25° C
  2. filtrationThe resultant white precipitate was collected by filtration
  3. washwashed with small amounts of EtOH, diethyl ether, and hexanes
  4. customdried in vacuo

Sources & evidence

ORD record
ord-43ffbc79b4814ca489ee6e3141beab3f
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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