Lawesson's reagent → HCID 50916207, compound

HRID 1374532Notes

Reaction equation

HRID 1374532 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])(=O)[NH2:24]>C1(C)C=CC=CC=1>[C:23]([C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])(=[S:10])[NH2:24]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 6950961cbz-l-prolinamide

Product 1

HCID 50916207HCID 50916207, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Part A. Lawesson's reagent (90 mg, 0.22 mmol) was added to a stirred slurry of benzyl (S)-2-carbamoyl-pyrrolidine-1-carboxylate (100 mg, 0.40 mmol) in toluene (3 mL) at ambient temperature. The reaction mixture was heated to 100° C. for 3 h then the solvents were removed. The residue was purified by flash silica gel chromatography yielding benzyl (S)-2-thiocarbamoylpyrrolidine-1-carboxylate as white solid (108 mg, crude quantative yield): HPLC (method 1) tR=2.55 min, Purity 100%; LCMS (method 4) tR=1.34 min, m/z 287 (M+H).

Workup

  1. customthe solvents were removed
  2. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-3085adb8810642d28fbbc97fcefa267a
Source dataset
uspto-grants-2007_01
Patent number
US07166586B2

Reaction notes

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