Sodium Hydroxide → [3-{1-[(Benzyloxy)carbonyl]piperidin-4-yl}-2-oxotetrahydropyrimidin-1(2H)-yl]acetic acid

HRID 20234Notes

Reaction equation

HRID 20234 reaction equation
[OH-].[Na+].C([O:7][C:8]([CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][N:13]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:19][CH2:18]2)[C:12]1=[O:33])=[O:9])(C)(C)C>C(O)C>[CH2:26]([O:25][C:23]([N:20]1[CH2:19][CH2:18][CH:17]([N:13]2[CH2:14][CH2:15][CH2:16][N:11]([CH2:10][C:8]([OH:9])=[O:7])[C:12]2=[O:33])[CH2:22][CH2:21]1)=[O:24])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68417510benzyl 4-[3-(tert-butoxycarbonylmethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate

Product 1

HCID 22137504[3-{1-[(Benzyloxy)carbonyl]piperidin-4-yl}-2-oxotetrahydropyrimidin-1(2H)-yl]acetic acidYield 101.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous 4N sodium hydroxide solution (10 mL) was added to a solution of benzyl 4-[3-(tert-butoxycarbonylmethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate (1.7 g) obtained in Example 35a) in ethanol (20 mL), and the mixture was stirred at room temperature overnight. Ethanol was distilled off under reduced pressure, and 1N hydrochloric acid was added to the residue to adjust pH to 3, followed by extraction with chloroform. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the title compound (1.5 g, quantitative) as a white powder.

Workup

  1. distillationEthanol was distilled off under reduced pressure, and 1N hydrochloric acid
  2. additionwas added to the residue
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ef18dcd08c242a3b02191fe8617a818
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

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