Sodium Hydroxide → {9-[(Phenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid

HRID 51356Notes

Reaction equation

HRID 51356 reaction equation
[C:1]1([CH2:7][N:8]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][C:23]([O:25]C)=[O:24])[C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][C:13]=3[C:27](=[O:29])[NH2:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([CH2:7][N:8]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][C:23]([OH:25])=[O:24])[C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][C:13]=3[C:27](=[O:29])[NH2:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 101783439-[(Phenyl)methyl]-5-carbamoylcarbazol-4-yloxyacetic acid, methyl ester

Product 1

HCID 9864359{9-[(Phenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acidYield 72.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the {9-[(phenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester (10.1 mg, 0.025 mM) and 0.025 mL (0.025 mM) of 1 N NaOH in 3 mL of ethanol was stirred for 16 h at 25° C. The resultant white precipitate was collected by filtration, washed with a small amount of EtOH, then dried in vacuo to afford 7.1 mg (70%) of the {9-[(phenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, sodium salt as a white powder. 1H NMR (DMSO-d6) δ7.6 (d, 1H, J=8 Hz), 7.5-7.05 (m, 11H), 6.55 (d, 1H, J=8 Hz), 5.75 (s, 2H), and 4.3 (s, 2H). IR (KBr, cm−1) 3471, 1657, 1615, 1591, 1496, 1453, 1412, 1330, 1272, and 1151. MS (ES) m/e 373, 375, 397. Elemental Analyses for C22H17N2O4Na: C, 66.67; H, 4.29; N, 7.07. Found C, 66.75; H, 4.55; N, 6.83.

Workup

  1. filtrationThe resultant white precipitate was collected by filtration
  2. washwashed with a small amount of EtOH
  3. customdried in vacuo

Sources & evidence

ORD record
ord-139d7c0acea84481b199beb138492dac
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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