Sodium Hydroxide → HCID 67425121, compound

HRID 1799106Notes

Reaction equation

HRID 1799106 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[S:21][C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:19][C:18]=2[C:28]([O:30]CC)=[O:29])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO.O1CCCC1>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][N:13]([CH2:16][C:17]2[S:21][C:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[N:19][C:18]=2[C:28]([OH:30])=[O:29])[CH2:14][CH2:15]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67425241HCID 67425241, compound

Product 1

HCID 67425121HCID 67425121, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1 N NaOH (5.4 mL) was added to a solution of ethyl 5-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)-2-phenylthiazole-4-carboxylate (1.50 g, 3.6 mmol) in methanol (10 mL) and tetrahydrofuran (10 mL). The reaction mixture was stirred at room temperature for 16 h then concentrated in vacuo. H2O was added and the mixture was washed with EtOAC. The pH of the aqueous layer was adjusted to 5 by the addition of 1N HCl and the resulting ppt was collected by filtration, washed with H2O, and dried to give 5-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)-2-phenylthiazole-4-carboxylic acid as a white solid (0.9 g, 64% yield).

Workup

  1. concentrationthen concentrated in vacuo
  2. additionH2O was added
  3. washthe mixture was washed with EtOAC
  4. additionThe pH of the aqueous layer was adjusted to 5 by the addition of 1N HCl
  5. filtrationthe resulting ppt was collected by filtration
  6. washwashed with H2O
  7. customdried

Sources & evidence

ORD record
ord-04559c130af9481ca91242bb75c1f089
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

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