Sodium Hydroxide → HCID 21906429, compound

HRID 988667Notes

Reaction equation

HRID 988667 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([NH:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21]C)=[O:20])=[O:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+]>CO>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([NH:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([OH:21])=[O:20])=[O:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21906218HCID 21906218, compound

Product 1

HCID 21906429HCID 21906429, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of methyl 2-[4-Boc-piperazine-1-ylcarbonyl]aminobenzoate (2.42 g, 6.7 mmol) in methanol (15 mL) was added 5 N sodium hydroxide (15 mL). After 45 min, the solution was partially concentrated in vacuo to a volume of about 10 mL and the solution was diluted with water and washed with diethyl ether. The aqueous phase was then acidified with conc HCl and extracted with ethyl acetate. The ethyl acetate solution was then washed with brine, dried with MgSO4, filtered and concentrated in vacuo to give 2.03 g (87%) of an off-white solid.

Workup

  1. concentrationthe solution was partially concentrated in vacuo to a volume of about 10 mL
  2. additionthe solution was diluted with water
  3. washwashed with diethyl ether
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate solution was then washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a9b9e7685664900ad77c13f194529a6
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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