2-Amino-2-methyl-1,3-propanediol → 2-Acetamido-4-methylthiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide

HRID 900872Notes

Reaction equation

HRID 900872 reaction equation
[NH2:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].[C:8]([NH:11][C:12]1[S:13][C:14]([S:18](Cl)(=[O:20])=[O:19])=[C:15]([CH3:17])[N:16]=1)(=[O:10])[CH3:9].C(N(CC)CC)C>O1CCOCC1>[OH:4][CH2:3][C:2]([NH:1][S:18]([C:14]1[S:13][C:12]([NH:11][C:8](=[O:10])[CH3:9])=[N:16][C:15]=1[CH3:17])(=[O:19])=[O:20])([CH2:5][OH:6])[CH3:7]

Participants

5

Reactant 3

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 8471TriethylamineHCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chloride

Product 1

HCID 866071002-Acetamido-4-methylthiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amideYield 17.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-amino-2-methyl-1,3-propanediol (1.86 g, 17.7 mmol) in dioxane (20 ml) was added at 0° C. (ice water bath) commercially available 2-acetamido-4-methylthiazole-5-sulfonyl chloride (1.5 g, 5.89 mmol) and triethylamine (0.9 ml, 6 mmol). The light yellow suspension was stirred at room temperature for 17 h, and evaporated. The crude product was further purified by flash chromatography on silica gel (ethyl acetate/MeOH) and subsequent crystallization (dichloromethane/MeOH/hexane) to yield 2-acetamido-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide (0.33 g, 17%) as a white solid. MS (ISP) 322.2 [(M−H)−]; mp 201° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by flash chromatography on silica gel (ethyl acetate/MeOH) and subsequent crystallization (dichloromethane/MeOH/hexane)

Sources & evidence

ORD record
ord-a9ce17c8a93549289db806ef07a09870
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

Loading…