Chloroacetone → HCID 86594337, compound

HRID 1374533Notes

Reaction equation

HRID 1374533 reaction equation
Cl[CH2:2][C:3](=O)[CH3:4].[C:6]([C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])(=[S:8])[NH2:7]>C(Cl)(Cl)Cl>[CH3:4][C:3]1[N:7]=[C:6]([C@@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[S:8][CH:2]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 50916207HCID 50916207, compound

Product 1

HCID 86594337HCID 86594337, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Part A. Chloroacetone (36 mg, 0.37 mmol) was added to a solution of benzyl (S)-2-thiocarbamoyl-pyrrolidine-1-carboxylate (90 mg, 0.34 mmol) in dry chloroform (2 mL). The resulting solution was heated to reflux for 24 h then purified by preparative HPLC yielding benzyl (S)-2-(4-methylthiazol-2-yl)-pyrrolidine-1-carboxylate as a colorless oil (55 mg, 54% yield): HPLC (method 1) tR=3.11 min, Purity 100%; LCMS (method 4) tR=1.57 min, m/z 303 (M+H).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 24 h
  3. customthen purified by preparative HPLC

Sources & evidence

ORD record
ord-1b9ae4d13b38472bb9c89fa610ffaa92
Source dataset
uspto-grants-2007_01
Patent number
US07166586B2

Reaction notes

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