Di-tert-butyl dicarbonate → Ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate

HRID 1358546Notes

Reaction equation

HRID 1358546 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2].[C:13]([O:17][C:18]([O:20]C(OC(C)(C)C)=O)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][O:20][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])=[N:8][C:7]=1[CH3:12])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

Product 1

HCID 21911455Ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of ethyl-2-amino-4-methyl-thiazole-5-carboxylate (18.6 g, 100 mmol), di-t-butyldicarbonate (26.2 g, 120 mmol) and 4-dimethylaminopyridine (800 mg, 6.55 mmol) in dry tetrahydrofuran (300 mL) was stirred under nitrogen for 18 h. The solvent was evaporated in vacuo. The residue was suspended in dichloromethane (1 L) and filtered through a pad of celite. The filtrate was washed with 1 N aqueous HCl solution (300 mL, 2×), water and brine, dried (MgSO4), and concentrated in vacuo. The residue was triturated with hexanes. The solid was filtered and dried in vacuo to obtain the title compound (20 g, 72%) as a tan solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. filtrationfiltered through a pad of celite
  3. washThe filtrate was washed with 1 N aqueous HCl solution (300 mL, 2×), water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with hexanes
  7. filtrationThe solid was filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-e39e24441995411ca2a0c12a8d9798ae
Source dataset
uspto-grants-2003_07
Patent number
US06596746B1

Reaction notes

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