2-Acetamido-4-methylthiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide → 2-Amino-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide

HRID 900873Notes

Reaction equation

[OH:1][CH2:2][C:3]([NH:7][S:8]([C:11]1[S:15][C:14]([NH:16]C(=O)C)=[N:13][C:12]=1[CH3:20])(=[O:10])=[O:9])([CH2:5][OH:6])[CH3:4]>Cl>[OH:6][CH2:5][C:3]([NH:7][S:8]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH3:20])(=[O:10])=[O:9])([CH2:2][OH:1])[CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred suspension of 2-acetamido-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide (0.33 g, 1.02 mmol) in 6N hydrochloric acid (4 ml) was heated for 2 h at 80° C., evaporated., and saturated NaHCO3 solution (30 ml) was added. The mixture was extracted with ethyl acetate (3×50 ml), the combined organic layers washed with brine (30 ml) and dried (MgSO4). The crude product was further purified by crystallization (dichloromethane/MeOH/hexane) to yield the title compound (0.11 g, 38%) as a white solid. MS (ISP) 280.0 [(M−H)−]; mp 170° C.

Workup

customevaporated
addition, and saturated NaHCO3 solution (30 ml) was added
extractionThe mixture was extracted with ethyl acetate (3×50 ml)
washthe combined organic layers washed with brine (30 ml)
dry with materialdried (MgSO4)
customThe crude product was further purified by crystallization (dichloromethane/MeOH/hexane)

Sources & evidence

ORD record: ord-8d4a2942ebc54395a426452c166412e1
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361659B2

Reaction notes

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