Triethylamine → HCID 86607111, compound

HRID 900891Notes

Reaction equation

HRID 900891 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[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>[C:7]([NH:10][C:11]1[S:12][C:13]([S:17]([N:1]2[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]2)(=[O:18])=[O:19])=[C:14]([CH3:16])[N:15]=1)(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chlorideHCID 982104-Hydroxypyrrolidine

Product 1

HCID 86607111HCID 86607111, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (RS)-3-pyrrolidinol (0.51 g, 5.85 mmol) in THF (12 ml) was added at 0° C. (ice water bath) commercially available 2-acetamido-4-methylthiazole-5-sulfonyl chloride (1.0 g, 3.93 mmol) and triethylamine (0.6 ml, 4.32 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 (dichloromethane/MeOH) and subsequent crystallization (dichloromethane/MeOH/hexane) to yield (RS)-1-(2-acetamido-4-methyl-thiazole-5-sulfonyl)-pyrrolidin-3-ol (0.82 g, 68%) as a white solid. MS (ISP) 306.3 [(M+H)+]; mp 241° C.

Workup

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

Sources & evidence

ORD record
ord-cce583d436e94eb291ab7e3b61303903
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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