Methyl iodide → Sodium

HRID 619787Notes

Reaction equation

HRID 619787 reaction equation
N[C:2]1C=C2C(C=CC(S(O)(=O)=O)=C2)=CC=1.[Na:16].[H-].[Na+].[C:19]([NH:29][C:30]1[CH:39]=[C:38]2[C:33]([CH:34]=[CH:35][C:36]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:37]2)=[CH:32][CH:31]=1)([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].CI>CN(C=O)C>[C:19]([NH:29][C:30]1[CH:39]=[C:38]2[C:33]([CH:34]=[CH:35][C:36]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:37]2)=[CH:32][CH:31]=1)([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20].[C:19]([N:29]([CH3:2])[C:30]1[CH:39]=[C:38]2[C:33]([CH:34]=[CH:35][C:36]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:37]2)=[CH:32][CH:31]=1)([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20].[Na:16]

Participants

9

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 681247-Aminonaphthalene-2-sulfonic acidHCID 5360545Sodium3×HCID 21845734HCID 21845734, compound

Product 3

HCID 5360545SodiumHCID 21845724HCID 21845724, compoundHCID 21845734HCID 21845734, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

N-Cbz-7-Aminonaphthalene-2-sulfonic acid, sodium salt is prepared as described in EXAMPLE 39, Part A using 7-aminonaphthalene-2-sulfonic acid, sodium salt (3 g, 12.2 mmol) in place of 6-aminonaphthalene-2-sulfonic acid, sodium salt. A 60% dispersion of sodium hydride (0.21 g, 5.27 mmol) in mineral oil is washed with hexanes twice, suspended in 20 mL of DMF and the resulting suspension is cooled to 0° C. To this mixture is added the crude N-Cbz-7-aminonaphthalene-2-sulfonic acid, sodium salt (1 g, 2.64 mmol) in 15 mL of DMF. The reaction mixture is stirred for 10 min at 0° C. and then treated with methyl iodide (0.49 mL, 7.92 mmol). The resulting mixture is allowed to warm to room temperature with stirring overnight. The reaction mixture is worked up according to the similar procedure used in EXAMPLE 32, Part A to yield the crude N-Cbz-7-methylaminonaphthalene-2-sulfonic acid, sodium salt (0.88 g) as a beige solid. A mixture of the sulfonic acid, sodium salt (0.88 g, 2.23 mmol) is chlorinated as described in EXAMPLE 32, Part A. The crude product is purified by column chromatography in a gradient of 10% EtOAc/hexanes to 30% EtOAc/hexanes to afford the title compound (0.38 g, 0.97 mmol) as a beige solid.

Workup

  1. temperatureto warm to room temperature
  2. stirringwith stirring overnight

Sources & evidence

ORD record
ord-45a20f01ef21418788873d2da5bfd4fa
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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