Sodium Hydroxide → 4-{[(Benzyloxy)carbonyl]amino}-5-chloro-2-methoxybenzoic acid

HRID 1381491Notes

Reaction equation

HRID 1381491 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:26])[C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[CH:8][C:7]=1[O:24][CH3:25]>O1CCOCC1>[CH2:17]([O:16][C:14]([NH:13][C:9]1[C:10]([Cl:12])=[CH:11][C:6]([C:5]([OH:26])=[O:4])=[C:7]([O:24][CH3:25])[CH:8]=1)=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11142640HCID 11142640, compound

Product 1

HCID 144031724-{[(Benzyloxy)carbonyl]amino}-5-chloro-2-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

200 ml 2N aqueous sodium hydroxide solution is added dropwise to a stirred solution of 72.1 g of the benzoic acid methyl ester produced in step (b) in 800 ml dioxane. The mixture is stirred for 20 hours and the organic solvent removed under a vacuum. The residue is dissolved in water and adjusted to pH 5-6 with 3N hydrochloric acid. The heading compound is filtered off and washed with water. M.pt. 182°-183° (from methanol).

Workup

  1. customthe organic solvent removed under a vacuum
  2. dissolutionThe residue is dissolved in water
  3. filtrationThe heading compound is filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-f0b7cb2e551c4118addbfb318093c287
Source dataset
uspto-grants-1989_02
Patent number
US04803199

Reaction notes

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