Sodium Hydroxide → HCID 21304066, compound

HRID 51391Notes

Reaction equation

HRID 51391 reaction equation
[C:1]1([CH2:11][N:12]2[C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([O:25][CH2:26][C:27]([O:29]C)=[O:28])[C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][C:17]=3[C:31](=[O:33])[NH2:32])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([CH2:11][N:12]2[C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([O:25][CH2:26][C:27]([OH:29])=[O:28])[C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][C:17]=3[C:31](=[O:33])[NH2:32])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86756267{9-[(1-Naphthyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester

Product 1

HCID 21304066HCID 21304066, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the {9-[(1-naphthyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester (21 mg, 0.048 mM) and 0.05 mL (0.05 mM) of 1 N NaOH in 5 mL of ethanol was stirred for 20 hours at 25° C. The resultant white precipitate was collected by filtration, washed with a small amount of EtOH, then dried in vacuo to afford 17 mg (80%) of the {9-[(1-naphthyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, sodium salt as a white powder. 1H NMR (DMSO-d6) δ8.4 (d, 1H, J=8 Hz), 8.05 (d, 1H, J=8 Hz), 7.8 (d, 1H, J=8 Hz), 7.75-7.2 (m, 8H), 7.1 (d, 1H, J=8 Hz), 6.95 (d, 1H, J=8 Hz), 6.55 (d, 1H, J=8 Hz), 6.3 (d, 1H, J=8 Hz), 6.15 (s, 2H), and 4.4 (s, 2H). IR (KBr, cm−1) 1664, 1615, 1595, 1455, 1408, 1324, 1275, and 775. MS (ES) m/e 423, 425.

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-253e1b555d7b40c49c7668479d6dfa41
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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