Sodium Carbonate → 5-({[7-({2-[(7-{[(3-Carboxy-4-hydroxyphenyl)amino]sulfonyl}(2-naphthyl)) amino]-ethyl}-amino)(2-naphthyl)]sulfonyl}amino)-2-hydroxybenzoic acid

HRID 1791074Notes

Reaction equation

HRID 1791074 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][C:20]([NH:26][CH2:27][CH2:28][NH:29][C:30]4[CH:39]=[CH:38][C:37]5[C:32](=[CH:33][C:34]([S:40]([NH:43][C:44]6[CH:49]=[CH:48][C:47]([OH:50])=[C:46]([C:51]([O:53]C)=[O:52])[CH:45]=6)(=[O:42])=[O:41])=[CH:35][CH:36]=5)[CH:31]=4)=[CH:21][CH:22]=3)[CH:17]=2)(=[O:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].C(=O)([O-])[O-].[Na+].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>CN(C=O)C>[C:4]([C:3]1[CH:8]=[C:9]([NH:12][S:13]([C:16]2[CH:17]=[C:18]3[C:23]([CH:22]=[CH:21][C:20]([NH:26][CH2:27][CH2:28][NH:29][C:30]4[CH:31]=[C:32]5[C:37]([CH:36]=[CH:35][C:34]([S:40]([NH:43][C:44]6[CH:49]=[CH:48][C:47]([OH:50])=[C:46]([CH:45]=6)[C:51]([OH:53])=[O:52])(=[O:42])=[O:41])=[CH:33]5)=[CH:38][CH:39]=4)=[CH:19]3)=[CH:24][CH:25]=2)(=[O:14])=[O:15])[CH:10]=[CH:11][C:2]=1[OH:1])([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 22041851Methyl 2-hydroxy-5-[({7-[(2-{[7-({[4-hydroxy-3-(methoxycarbonyl)phenyl]amino}sulfonyl)(2-naphthyl)]amino}ethyl)amino](2-naphthyl)}sulfonyl)amino]benzoate

Product 1

HCID 184210795-({[7-({2-[(7-{[(3-Carboxy-4-hydroxyphenyl)amino]sulfonyl}(2-naphthyl)) amino]-ethyl}-amino)(2-naphthyl)]sulfonyl}amino)-2-hydroxybenzoic acidYield 40.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 64 mg (0.08 mmol) of compound 120 was added 20 mL of saturated sodium carbonate, 76 mg of sodium hydrosulfite (Na2S2O4), and 2 mL of DMF. The reaction was allowed to stir at ambient temperature for 22 hours. Then, the reaction was extracted with ethyl acetate and 1 N HCl. The organic layer was dried (MgSO4), filtered, and the volatiles removed by rotary evaporation. The product was purified by reverse-phase HPLC (C18, 250×20 mm column) using trifluoroacetic acid (TFA) buffer system (Buffer A: 5% acetonitrile, 95% water, 0.05% TFA; Buffer B: 95% acetonitrile, 5% water, 0.05% TFA; 17 mL/min; 0–50% B in 10 min., 50% B for 17 min., 50–100% B in 20 min). Fractions containing the product were combined and lyophilized to provide 24 mg of compound 121.

Workup

  1. extractionThen, the reaction was extracted with ethyl acetate and 1 N HCl
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customthe volatiles removed by rotary evaporation
  5. customThe product was purified by reverse-phase HPLC (C18, 250×20 mm column)
  6. wait0–50% B in 10 min.
  7. wait50% B for 17 min.
  8. wait50–100% B in 20 min)
  9. additionFractions containing the product

Sources & evidence

ORD record
ord-9ca64eda72ed45958f0f229fc7b46a78
Source dataset
uspto-grants-2006_07
Patent number
US07071231B2

Reaction notes

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