Hydrochloric Acid → 4-(Methoxycarbonyl)-alpha-methyl-1H-1,2,3-triazole-1-acetic acid

HRID 1888183Notes

Reaction equation

HRID 1888183 reaction equation
C([O:5][C:6](=[O:18])[CH:7]([N:9]1[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[N:11]=[N:10]1)[CH3:8])(C)(C)C.Cl>O1CCOCC1>[CH3:17][O:16][C:14]([C:12]1[N:11]=[N:10][N:9]([CH:7]([CH3:8])[C:6]([OH:18])=[O:5])[CH:13]=1)=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66839487methyl 1-(2-tert-butoxy-1-methyl-2-oxoethyl)-1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 120338024-(Methoxycarbonyl)-alpha-methyl-1H-1,2,3-triazole-1-acetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of 0.55 g (2.2 mmol) of methyl 1-(2-tert-butoxy-1-methyl-2-oxoethyl)-1H-1,2,3-triazole-4-carboxylate from step A in 3 mL of anhydrous 1,4-dioxane was added 2.7 mL (11 mmol) of a 4.0 M hydrogen chloride solution in 1,4-dioxane. The resulting mixture was stirred for 1 h and then evaporated to dryness to afford the title compound as an off-white solid (0.40 g, 93%). 1HNMR (500 MHz, CD3OD) δ: 8.67 (s, 1H), 5.60 (q, J=7.3 Hz, 1H), 3.90 (s, 3H), 1.88 (d, J=7.3 Hz, 3H). LC-MS: m/z (ES) 200 (MH)+.

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-0df17751b63a4b24ac52ae87486a0882
Source dataset
uspto-grants-2013_08
Patent number
US08501786B2

Reaction notes

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