Sodium Hydroxide → HCID 66997971, compound

HRID 537411Notes

Reaction equation

HRID 537411 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH:12]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:13]([N:15]2[CH2:20][CH2:19][CH:18]([CH3:21])[CH2:17][CH2:16]2)=[O:14])[CH:5]=1.[OH-].[Na+]>CO.O1CCOCC1>[C:26]([O:25][C:23]([NH:22][CH:12]([C:13]([N:15]1[CH2:16][CH2:17][CH:18]([CH3:21])[CH2:19][CH2:20]1)=[O:14])[CH2:11][CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:30])=[O:2])=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66997911HCID 66997911, compound

Product 1

HCID 66997971HCID 66997971, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Procedure

A solution of 90 mg (0.22 mmol) of 3-[3-tert-butoxycarbonylamino-4-(4-methyl-piperidin-1-yl)-4-oxo-butyl]-benzoic acid methyl ester (prepared in the synthesis of Example 77) in 1 mL of 1:1 MeOH/1,4-dioxane and 0.5 mL of 1 N NaOH is stirred for 3 h. The organic phase is separated and suspended in 2 mL of water. The pH is adjusted to 2 with HCl, and the resulting precipitate is filtered to provide 85 mg (98%) of 3-[3-tert-butoxycarbonylamino-4-(4-methyl-piperidin-1-yl)-4-oxo-butyl]-benzoic acid.

Workup

  1. customThe organic phase is separated
  2. filtrationthe resulting precipitate is filtered

Sources & evidence

ORD record
ord-6a802ee3beff438582143e0761c96940
Source dataset
uspto-grants-2014_10
Patent number
US08859814B2

Reaction notes

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