Sodium Hydroxide → 2-Tert-butoxycarbonylamino-5-[(3-carboxyphenyl)thio]thiazole

HRID 49138Notes

Reaction equation

HRID 49138 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[S:12][C:13]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([O:25]C)=[O:24])[CH:18]=2)=[CH:14][N:15]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO.C1COCC1>[CH3:5][C:3]([CH3:6])([O:7][C:8]([NH:10][C:11]1[S:12][C:13]([S:16][C:17]2[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=2)[C:23]([OH:25])=[O:24])=[CH:14][N:15]=1)=[O:9])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 221704102-Tert-butoxycarbonylamino-5-[(3-carbomethoxyphenyl)thio]thiazole

Product 1

HCID 221704202-Tert-butoxycarbonylamino-5-[(3-carboxyphenyl)thio]thiazole

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A 1 N aqueous sodium hydroxide solution (50 mL, 50 mmol) was added dropwise to a stirred solution of 2-tert-butoxycarbonylamino-5-[(3-carbomethoxyphenyl)thio]thiazole (1.8 g, (contaminated with bis(tert-butoxycarbonyl)amino adduct)) in a methanol-THF mixture (160 mL, 3:1). The solution was stirred at rt. for 24 h and concentrated. The residue was acidified with 2 N aqueous HCl (30 mL) and the suspension was extracted with dichloromethane-methanol mixture (120 mL, 3:1, 2×). The combined organic extract was dried (MgSO4), filtered and concentrated in vacuo to obtain the titled compound (1.32 g, 75% overall yield from Example 1, part A) as an off-white solid.

Workup

  1. concentrationconcentrated
  2. extractionthe suspension was extracted with dichloromethane-methanol mixture (120 mL, 3:1, 2×)
  3. extractionThe combined organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dcaf7ef49c6e461b954ec64cb251cdb9
Source dataset
uspto-grants-2004_03
Patent number
US06706717B2

Reaction notes

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