Tetrahydrofuran → 2-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}-1,3-thiazole-5-carboxylic acid

HRID 2043720Notes

Reaction equation

HRID 2043720 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4].O1CCCC1.[OH-].[Na+]>CO>[C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[N:7][CH:6]=1)([OH:4])=[O:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 600321491,1-Dimethylethyl 4-[5-(methoxycarbonyl)-2-thiazolyl]-1-piperazinecarboxylate2×

Product 1

HCID 672940122-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,1-Dimethylethyl 4-[5-(methoxycarbonyl)-2-thiazolyl]-1-piperazinecarboxylate (i.e. the product of Example 4, Step A) (2.56 g, 8 mmol) in 15 mL of methanol and 15 mL of tetrahydrofuran was added 1 N aqueous NaOH solution (10 mL), and the mixture was stirred at ambient temperature overnight. The mixture was concentrated under reduced pressure, diluted with water, washed with ether, and acidified with excess 20% aqueous citric acid solution to give a precipitate. The precipitate was filtered, washed with water and dried to give 2.12 g of the title compound as a slightly pink solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. washwashed with ether
  4. customto give a precipitate
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-f14f6c6769944e9da88ce894b60a52db
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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