Sodium Hydroxide → HCID 14403497, compound

HRID 1195007Notes

Reaction equation

HRID 1195007 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:17]2[CH2:16][CH:15]([C:18]([O:20]CC)=[O:19])[N:14]([C:23](=[O:37])[CH:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:13][C:12]=2[N:11]=[CH:10]1.[OH-].[Na+]>C1COCC1.CO.Cl.CO.O>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:17]2[CH2:16][CH:15]([C:18]([OH:20])=[O:19])[N:14]([C:23](=[O:37])[CH:24]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:13][C:12]=2[N:11]=[CH:10]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 14457543HCID 14457543, compound

Product 1

HCID 14403497HCID 14403497, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 21899815MeOH tetrahydrofuranSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

A solution of the product from Example 16 (2.35 g) in 25 mL THF-methanol (2:1) is treated with 10 mL 1N NaOH, stirring 90 min at 25° C. After treatment with 10 mL 1N HCl, the mixture is diluted with 60 mL methanol-water (2:1) and concentrated in vacuo until a thick slurry forms. The slurry is diluted with water and the desired carboxylic acid is collected by filtration. MS (FAB) 468 (M+1); mp 187°-190° C.

Workup

  1. concentrationconcentrated in vacuo until a thick slurry forms
  2. additionThe slurry is diluted with water
  3. filtrationthe desired carboxylic acid is collected by filtration

Sources & evidence

ORD record
ord-16023e03466542f7acdf1181e4b97897
Source dataset
uspto-grants-1989_03
Patent number
US04816463

Reaction notes

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