Sodium Hydroxide → HCID 178454312, compound

HRID 233489Notes

Reaction equation

HRID 233489 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:19][CH2:20][CH2:21][C:22]([O:24]C)=[S:23])[C:9]([NH2:18])=[N:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]([CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[S:23])[C:9]([NH2:18])=[N:10][C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54296086HCID 54296086, compound

Product 1

HCID 178454312HCID 178454312, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of methyl [2-(N,N'-di-tert-butyloxycarbonylguanidino)ethyl]thioacetate (1.24 g, 3.17 mmol) in ethanol (15 mL) at room temperature (15 mL) was added 10% aqueous sodium hydroxide solution (3 mL). After 2 h, the mixture was concentrated, and the residue was treated with 10% aqueous HCl solution. The resulting mixture was extracted with ethyl acetate, and the organic extracts were washed with water and brine, dried over sodium sulfate, and concentrated to afford 1.06 g of [2-(N,N'-di-tert-butyloxycarbonylguanidino)ethyl]thioacetic acid as a white solid. 1H NMR (CDCl3) δ1.50 (s, 18), 2.89 (t, 2, J=8), 3.34 (s, 2), 3.72 (m, 2), 8.82 (br s, 2).

Workup

  1. concentrationthe mixture was concentrated
  2. additionthe residue was treated with 10% aqueous HCl solution
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe organic extracts were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ce64e1a4153a477e91db12c4bdcfb50d
Source dataset
uspto-grants-1997_01
Patent number
US05593986

Reaction notes

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