Triethylamine → HCID 86607107, compound

HRID 900883Notes

Reaction equation

HRID 900883 reaction equation
[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].[C:7]([NH:10][C:11]1[S:12][C:13]([S:17](Cl)(=[O:19])=[O:18])=[C:14]([CH3:16])[N:15]=1)(=[O:9])[CH3:8].C(N(CC)CC)C>C1COCC1>[OH:4][CH2:3][CH:2]([NH:1][S:17]([C:13]1[S:12][C:11]([NH:10][C:7](=[O:9])[CH3:8])=[N:15][C:14]=1[CH3:16])(=[O:18])=[O:19])[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68294SerinolHCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chloride

Product 1

HCID 86607107HCID 86607107, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-amino-1,3-propanediol (2.15 g, 23.6 mmol) in THF (26 ml) was added at 0° C. (ice water bath) commercially available 2-acetamido-4-methylthiazole-5-sulfonyl chloride (2.0 g, 7.85 mmol) and triethylamine (1.2 ml, 8.64 mmol). The light yellow suspension was stirred at room temperature for 17 h, and evaporated. The crude product was further purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 80:10:1) to yield 2-acetamido-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-ethyl)-amide (1.46 g, 60%) as a light yellow solid. MS (ISP) 308.1 [(M−H)−]; mp 217° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 80:10:1)

Sources & evidence

ORD record
ord-299ccea4a13244a8b15997c147a2a91f
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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