Sodium Hydroxide → HCID 67365959, compound

HRID 619832Notes

Reaction equation

HRID 619832 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C[O:9][C:10](=[O:45])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[N:20][NH2:21])=[CH:15][C:14]=1[CH2:22][N:23]1[CH2:27][CH2:26][CH:25]([NH:28][S:29]([C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][C:36]([O:42][CH3:43])=[CH:37][CH:38]=3)[CH:33]=2)(=[O:31])=[O:30])[C:24]1=[O:44].[OH-].[Na+]>CCO>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:21][N:20]=[CH:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:10]([OH:45])=[O:9])=[C:14]([CH2:22][N:23]2[CH2:27][CH2:26][CH:25]([NH:28][S:29]([C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][C:36]([O:42][CH3:43])=[CH:37][CH:38]=4)[CH:33]=3)(=[O:31])=[O:30])[C:24]2=[O:44])[CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67365717HCID 67365717, compound

Product 1

HCID 67365959HCID 67365959, compoundYield 388.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of {4-(aminoiminomethyl)-2-[3-(7-methoxynaphthalene-2-sulfonylamino)-2-oxopyrrolidin-1-ylmethyl]-phenoxy}-acetic acid methyl ester trifluoroacetate (0.1 g, 0.18 mmol), prepared as in EXAMPLE 120, Part F, in 2 mL of EtOH is added 10 N NaOH (0.05 mL). The solution is stirred for 5 hours. After this time, the solution is concentrated. The residue is dissolved in 2 mL of H2O and the pH is adjusted to 3 using 1 N HCl. The solid which forms is collected by filtration. The solid is purified by RP-HPLC eluting with a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN. The appropriate fraction are lyophilized to afford the title compound (0.05 g, 0.7 mmol) as a white solid.

Workup

  1. concentrationAfter this time, the solution is concentrated
  2. dissolutionThe residue is dissolved in 2 mL of H2O
  3. filtrationThe solid which forms is collected by filtration
  4. customThe solid is purified by RP-HPLC
  5. washeluting with a gradient of 10% CH3CN/H2O (0.1% TFA) to 100% CH3CN

Sources & evidence

ORD record
ord-70467dd7059a4301b66c286f2aaaa003
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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